Andre Agassi College Preparatory Academy

Andre Kirk Agassi ( ; born April 29, 1970) is an American former world No. 1 tennis player. He is an eight-time major champion and an Olympic gold medalist, as well as a runner-up in seven other majors.

Agassi is the second of five men to achieve the career Grand Slam in the Open Era and the fifth of eight overall to make the achievement. He is also the first of two men to achieve the career Golden Slam (career Grand Slam and Olympic gold medal), as well as the only man to win a career Super Slam (career Grand Slam, plus the Olympic gold medal and the year-end championships).

Agassi was the first man to win all four singles majors on three different surfaces (hard, clay and grass), and remains the most recent American man to win the French Open (in 1999) and the Australian Open (in 2003). He also won 17 Masters titles and was part of the winning Davis Cup teams in 1990, 1992 and 1995. Agassi reached the world No. 1 ranking for the first time in 1995, but was troubled by personal issues during the mid-to-late 1990s and sank to No. 141 in 1997, prompting many to believe that his career was over. Agassi returned to No. 1 in 1999 and enjoyed the most successful run of his career over the next four years. During his 20-plus year tour career, Agassi was known by the nickname "The Punisher".

After suffering from sciatica caused by two bulging discs in his back, a spondylolisthesis ( vertebral displacement) and a bone spur that interfered with the nerve, Agassi retired from professional tennis on September 3, 2006, after losing in the third round of the US Open. He is the founder of the Andre Agassi Charitable Foundation, which has raised over $60 million for at-risk children in Southern Nevada. In 2001, the Foundation opened the Andre Agassi College Preparatory Academy in Las Vegas, a K–12 public charter school for at-risk children. He has been married to fellow tennis player Steffi Graf since 2001.

Early life

Andre Agassi was born in Las Vegas, Nevada, to Emmanuel "Mike" Agassi (Aghassian), a former Olympic boxer from Iran and American Elizabeth "Betty" Agassi (née Dudley). His father is of Armenian and Assyrian heritage. Andre Agassi's mother, Betty, is a breast cancer survivor. He has three older siblings – Rita (last wife of former number one Pancho Gonzales), Philip and Tami. Andre was given the middle name Kirk after Kirk Kerkorian, an Armenian American billionaire. Emmanuel Agassi, then a waiter at Tropicana Las Vegas, had met Kerkorian in 1963.

At the age of 12, Agassi and his good friend and doubles partner, Roddy Parks, won the 1982 National Indoor Boys 14s Doubles Championship in Chicago. Agassi describes memorable experiences and juvenile pranks with Roddy in his book ''Open''.

When he was 13, Agassi was sent to Nick Bollettieri's Tennis Academy in Florida. He was meant to stay for only three months, because that was all his father could afford. After thirty minutes of watching Agassi play, Bollettieri, deeply impressed by his talent, called Mike and said: "Take your check back. He's here for free." Agassi then dropped out of school in the ninth grade to pursue a full-time tennis career.

Professional career

1986–1993: Breakthrough and the first major title

Agassi turned professional at the age of 16 and competed in his first tournament at La Quinta, California. He won his first match against John Austin, but then lost his second match to Mats Wilander. By the end of 1986, Agassi was ranked No. 91. He won his first top-level singles title in 1987 at the Sul American Open in Itaparica and ended the year ranked No. 25. He won six additional tournaments in 1988 (Memphis, U.S. Men's Clay Court Championships, Forest Hills WCT, Stuttgart Outdoor, Volvo International and Livingston Open), and, by December of that year, he had surpassed US$1 million in career prize money after playing in just 43 tournaments—the fastest anyone in history had reached that level. During 1988, he also set the open-era record for most consecutive victories by a male teenager (a record that stood for 17 years until Rafael Nadal broke it in 2005). His year-end ranking was No. 3, behind second-ranked Ivan Lendl and top-ranked Mats Wilander. Both the Association of Tennis Professionals and ''Tennis'' magazine named Agassi the Most Improved Player of the Year for 1988.

In addition to not playing the Australian Open (which later became his best Grand Slam event) for the first eight years of his career, Agassi chose not to play at Wimbledon from 1988 through 1990 and publicly stated that he did not wish to play there because of the event's traditionalism, particularly its "predominantly white" dress code to which players at the event are required to conform.

Strong performances on the tour meant that Agassi was quickly tipped as a future Grand Slam champion. While still a teenager, he reached the semi-finals of both the French Open and the US Open in 1988 and made the US Open semi-finals in 1989. He began the 1990s with a series of near-misses. He reached his first Grand Slam final in 1990 at the French Open, where he was favored before losing in four sets to Andrés Gómez, which he later attributed in his book to worrying about his wig falling off during the match. He reached his second Grand Slam final of the year at the US Open, defeating defending champion Boris Becker in the semi-finals. His opponent in the final was Pete Sampras; a year earlier, Agassi had crushed Sampras, after which time he told his coach that he felt bad for Sampras because he was never going to make it as a pro. Agassi lost the US Open final to Sampras in three sets. The Agassi-Sampras rivalry became the biggest one in tennis over the rest of the decade. Agassi ended 1990 on a high note as he helped the United States win its first Davis Cup in 8 years and won his only Tennis Masters Cup, beating reigning Wimbledon champion Stefan Edberg in the final.

In 1991, Agassi reached his second consecutive French Open final, where he faced fellow Bollettieri Academy alumnus Jim Courier. Courier emerged the victor in a five-set final. Agassi decided to play at Wimbledon in 1991, leading to weeks of speculation in the media about the clothes he would wear. He eventually emerged for the first round in a completely white outfit. He reached the quarterfinals on that occasion, losing in five sets to David Wheaton.

Agassi's Grand Slam tournament breakthrough came at Wimbledon, not at the French Open or the US Open, where he had previously enjoyed success. In 1992, he defeated Goran Ivanišević in a five-set final. Along the way, Agassi overcame two former Wimbledon champions: Boris Becker and John McEnroe. No other baseliner would triumph at Wimbledon until Lleyton Hewitt ten years later. Agassi was named the BBC Overseas Sports Personality of the Year in 1992. Agassi once again played on the United States' Davis Cup winning team in 1992. It was their second Davis cup title in three years. Agassi famously played the game wearing Oakley brand sunglasses, and a photo of him from the day appeared on the cover of ''Tennis'' magazine. In his memoir, he wrote that he was covering up bloodshot eyes from a hangover and claimed that the founder of Oakley, Jim Jannard, had sent him a Dodge Viper to thank him for the inadvertent publicity.

In 1993, Agassi won the only doubles title of his career, at the Cincinnati Masters, partnered with Petr Korda. He missed much of the early part of that year due to injuries. Although he made the quarterfinals in his Wimbledon title defense, he lost to eventual champion and No. 1 Pete Sampras in five sets. Agassi lost in the first round at the US Open to Thomas Enqvist and required wrist surgery late in the year.

1994–1997: Rise to the top, Olympic Gold and the fall

With new coach Brad Gilbert on board, Agassi began to employ more of a tactical, consistent approach, which fueled his resurgence. He started slowly in 1994, losing in the first week at the French Open and Wimbledon. Nevertheless, he emerged during the hard-court season, winning the Canadian Open. His comeback culminated at the 1994 US Open with a five-set fourth-round victory against Michael Chang. He then became the first man to capture the US Open as an unseeded player, beating Michael Stich in the final. Along the way, he beat 5 seeded players.

In 1995, Agassi shaved his balding head, breaking with his old "image is everything" style. He competed in the 1995 Australian Open (his first appearance at the event) and won, beating defending champion Sampras in a four-set final. Agassi and Sampras met in five tournament finals in 1995, all on hardcourt, with Agassi winning three. Agassi won three Masters Series events in 1995 ( Cincinnati, Key Biscayne, and the Canadian Open) and seven titles total. He compiled a career-best 26-match winning streak during the summer hard-court circuit, with the last victory being in an intense late-night four-set semi-final of the US Open against Boris Becker. The streak ended the next day when Agassi lost the final to Sampras. Agassi admitted this loss, which gave Sampras a 9–8 lead in their head-to-head meetings, took two years for him to get over it mentally.

Agassi reached the world No. 1 ranking for the first time in April 1995. He held that ranking until November, for a total of 30 weeks. Agassi skipped most of the fall indoor season which allowed Sampras to surpass him and finish ranked No. 1 at the year-end ranking. In terms of win–loss record, 1995 was Agassi's best year. He won 73 and lost 9 matches, and was also once again a key player on the United States' Davis Cup winning team—the third and final Davis Cup title of his career.

1996 was a less successful year for Agassi, as he failed to reach any Grand Slam final. He suffered two early-round losses to Chris Woodruff and Doug Flach at the French Open and Wimbledon, respectively, and lost to Chang in straight sets in the Australian and US Open semi-finals. At the time, Agassi blamed the Australian Open loss on the windy conditions, but later said in his biography that he had lost the match on purpose, as he did not want to play Boris Becker, whom he would have faced in that final. The high point for Agassi was winning the men's singles gold medal at the Olympic Games in Atlanta, beating Sergi Bruguera of Spain in the final. Agassi also successfully defended his singles titles in Cincinnati and Key Biscayne.

1997 was the low point of Agassi's career. His wrist injury resurfaced, and he played only 24 matches during the year. He later confessed that he started using crystal methamphetamine at that time, allegedly on the urging of a friend. He failed an ATP drug test, but wrote a letter claiming the same friend had spiked a drink. The ATP dropped the failed drug test as a warning. In his autobiography, Agassi admitted that the letter was a lie. He quit the drug soon after. At this time Agassi was also in a failing marriage with actress, model, and socialite Brooke Shields and had lost interest in the game. He won no top-level titles, and his ranking sank to No. 141 on November 10, 1997, prompting many to believe that his run as one of the sport's premier competitors was over and he would never again win any significant championships.

1998–2003: Return to glory and Career Super Slam

In 1998, Agassi began a rigorous conditioning program and worked his way back up the rankings by playing in Challenger Series tournaments, a circuit for pro players ranked outside the world's top 50. After returning to top physical and mental shape, Agassi recorded the most successful period of his tennis career and also played classic matches in that period against Pete Sampras and Patrick Rafter.

In 1998, Agassi won five titles and leapt from No. 110 to No. 6, the highest jump into the top 10 made by any player during a calendar year. At Wimbledon, he had an early loss in the second round to Tommy Haas. He won five titles in ten finals and was runner-up at the Masters Series tournament in Key Biscayne, losing to Marcelo Ríos, who became No. 1 as a result. At the year end he was awarded the ATP Most Improved Player of the Year for the second time in his career (the first being 10 years earlier in 1988).

Agassi entered the history books in 1999 when he came back from two sets to love down to beat Andrei Medvedev in a five-set French Open final, becoming, at the time, only the fifth male player (joining Rod Laver, Fred Perry, Roy Emerson and Don Budge—these have since been joined by Roger Federer, Rafael Nadal, and Novak Djokovic) to win all four Grand Slam singles titles during his career. Only Laver, Agassi, Federer, Nadal and Djokovic have achieved this feat during the Open Era. This win also made him the first (of only four, the next being Federer, Nadal and Djokovic respectively) male player in history to have won all four Grand Slam titles on three different surfaces (clay, grass and hard courts). Agassi also became the only male player to win the Career Super Slam, consisting of all four Grand Slam tournaments plus an Olympic gold medal in singles and a Year-end championship.

Agassi followed his 1999 French Open victory by reaching the Wimbledon final, where he lost to Sampras in straight sets. He rebounded from his Wimbledon defeat by winning the US Open, beating Todd Martin in five sets (rallying from a two sets to one deficit) in the final. Overall during the year Agassi won 5 titles including two majors and the ATP Masters Series in Paris, where he beat Marat Safin. Agassi ended 1999 as the No. 1, ending Sampras's record of six consecutive year-ending top rankings (1993–98). This was the only time Agassi ended the year at No. 1. Agassi was runner-up to Sampras at the year-end Tennis Masters Cup losing 1–6, 5–7, 4–6 despite beating Sampras in the round-robin 6–2, 6–2.

He began the next year 2000 by capturing his second Australian Open title, beating Sampras in a five-set semi-final and Yevgeny Kafelnikov in a four-set final. He was the first male player to have reached four consecutive Grand Slam finals since Rod Laver achieved the Grand Slam in 1969. At the time, Agassi was also only the fourth player since Laver to be the reigning champion of three of four Grand Slam events, missing only the Wimbledon title.. 2000 also saw Agassi reach the semi-finals at Wimbledon, where he lost in five sets to Rafter in a match considered by many to be one of the best ever at Wimbledon. At the inaugural Tennis Masters Cup in Lisbon, Agassi reached the final after defeating Marat Safin in the semi-finals to end the Russian's hopes to become the youngest No. 1 in the history of tennis. Agassi then lost to Gustavo Kuerten in the final, allowing Kuerten to be crowned year-end No. 1.

Agassi opened 2001 by successfully defending his Australian Open title with a straight-sets final win over Arnaud Clément. En route, he beat a cramping Rafter in five sets in front of a sell-out crowd in what turned out to be the Aussie's last Australian Open. At Wimbledon, they met again in the semi-finals, where Agassi lost another close match to Rafter, 8–6 in the fifth set. In the quarterfinals at the US Open, Agassi lost a 3-hour, 33 minute epic match with Sampras, 7–6, 6–7, 6–7, 6–7, with no breaks of serve during the 52-game match. Despite the setback, Agassi finished 2001 ranked No. 3, becoming the only male tennis player to finish a year ranked in the top 3 in three different decades.

2002 opened with disappointment for Agassi, as injury forced him to skip the Australian Open, where he was a two-time defending champion. Agassi recovered from the injury and later that year defended his Key Biscayne title beating then rising Roger Federer in a four-set final. At the US Open, Agassi overcame No.1 ranked and defending champion Lleyton Hewitt in the semi-finals. This led to what turned out to be the last duel between Agassi and Sampras in final of the US Open, which Sampras won in four sets and left Sampras with a 20–14 edge in their 34 career meetings. The match was the last of Sampras's career. Agassi's US Open finish, along with his Masters Series victories in Key Biscayne, Rome and Madrid, helped him finish 2002 as the oldest year-end No. 2 at 32 years and 8 months.

In 2003, Agassi won the eighth (and final) Grand Slam title of his career at the Australian Open, where he beat Rainer Schüttler in straight sets in the final.

On April 28, 2003, he recaptured the No. 1 ranking to become the oldest top-ranked male player since the ATP rankings began at 33 years and 13 days. The record was later surpassed by Roger Federer in 2018. He had held the No. 1 ranking for two weeks, when Lleyton Hewitt took it back on May 12, 2003. Agassi then recaptured the No. 1 ranking once again on June 16, 2003, which he held for 12 weeks until September 7, 2003. There he managed to reach the US Open semi-finals, where he lost to Juan Carlos Ferrero, surrendering his No. 1 ranking to him. During his career, Agassi held the ranking for a total of 101 weeks. Agassi's ranking slipped when injuries forced him to withdraw from a number of events. At the year-end Tennis Masters Cup, Agassi lost in the final to Federer, his third time to finish as runner-up in the event after losses in 1999 and 2000, and finished the year ranked No. 4. At age 33, he had been one of the oldest players to rank in the top 5 since Connors, at age 35, was No. 4 in 1987.

2004–2006: Final years

Agassi in 2006
In 2004, Agassi began the year with a five-set loss in the semi-finals of the Australian Open to Marat Safin; the loss ended Agassi's 26-match winning streak at the event. He won the Masters series event in Cincinnati to bring his career total to 59 top-level singles titles and a record 17 ATP Masters Series titles, having already won seven of the nine ATP Masters tournament—all except the tournaments in Monte Carlo and Hamburg. At 34, he became the second-oldest singles champion in Cincinnati tournament history (the tournament began in 1899), tied with Roger Federer and surpassed only by Ken Rosewall, who won the title in 1970 at age 35. He finished the year ranked No. 8, one of the oldest players to finish in the top 10 since the 36-year-old Connors was No. 7 in 1988. At the time, Agassi also became the sixth male player during the open era to reach 800 career wins with his first-round victory over Alex Bogomolov in Countrywide Classic in Los Angeles.

Agassi's 2005 began with a quarterfinal loss to Federer at the Australian Open. Agassi had several other deep runs at tournaments, but had to withdraw from several events due to injury. He lost to Jarkko Nieminen in the first round of the French Open. He won his fourth title in Los Angeles and reached the final of the Rogers Cup, before falling to No. 2 Rafael Nadal.

Agassi's 2005 was defined by an improbable run to the US Open final. After beating Răzvan Sabău and Ivo Karlović in straight sets and Tomáš Berdych in four sets, Agassi won three consecutive five-set matches to advance to the final. The most notable of these matches was his quarterfinal victory over James Blake, where he rallied from two sets down to win in the fifth set tie-breaker. His other five-set victories were on Xavier Malisse in the fourth round and Robby Ginepri in the semi-finals. In the final, Agassi faced Federer, who was seeking his second consecutive US Open title and his sixth Grand Slam title in two years. Federer defeated Agassi in four sets. Agassi finished 2005 ranked No. 7, his 16th time in the year-end top-10 rankings, which tied Connors for the most times ranked in the top 10 at year's end.

Agassi had a poor start to 2006, as he was still recovering from an ankle injury and also suffering from back and leg pain and lack of match play. Agassi withdrew from the Australian Open because of the ankle injury, and his back injury and other pains forced him to withdraw from several other events, eventually skipping the entire clay-court season including the French Open. This caused his ranking to drop out of the top 10 for the last time. Agassi returned for the grass-court season, playing a tune-up, and then Wimbledon. He was defeated in the third round by world No. 2 (and eventual runner-up) Rafael Nadal. Against conventions, Agassi, the losing player, was interviewed on court after the match. At Wimbledon, Agassi announced his plans to retire following the US Open. Agassi played only two events during the summer hard-court season with his best result being a quarterfinal loss at the Countrywide Classic in Los Angeles to Fernando González of Chile, which resulted in him being unseeded at the US Open.

Agassi had a short, but dramatic, run in his final US Open. Because of extreme back pain, Agassi was forced to receive anti-inflammatory injections after every match. After a tough four-set win against Andrei Pavel, Agassi faced eighth-seeded Marcos Baghdatis in the second round who had earlier advanced to the 2006 Australian Open final and Wimbledon semi-finals. Agassi won in five tough sets as the younger Baghdatis succumbed to muscle cramping in the final set. In his last match, Agassi fell to 112th-ranked big-serving Benjamin Becker of Germany in four sets. Agassi received a four-minute standing ovation from the crowd after the match and delivered a retirement speech.

Rivalries

Agassi vs. Sampras

The rivalry has been called the greatest of the generation of players competing in the 1990s, as Sampras and Agassi were the most successful players of that decade. They also had very contrasting playing styles, with Sampras being considered the greatest server and Agassi the greatest serve returner at the time. Agassi and Sampras met 34 times on the tour level with Agassi trailing 14–20.

The 1990 US Open was their first meeting in a Grand Slam tournament final. Agassi was favored as he was ranked No. 4 at the time, compared to the No. 12 ranking of Sampras and because Agassi had defeated Sampras in their only previously completed match. Agassi, however, lost the final to Sampras in straight sets. Their next meeting in a Grand Slam was at the 1992 French Open, where they met in the quarterfinals. Although Sampras was ranked higher, Agassi came out winning in straight sets. They met again on a Grand Slam level at the quarterfinals of Wimbledon in 1993, where Agassi was the defending champion and Sampras was the newly minted world No. 1. Agassi dug himself out from a two-sets-to-love hole, levelling the match at two sets apiece; however, Sampras prevailed in five sets, and went on to win his first Wimbledon championship.

With both Sampras and Agassi participating, the US won the Davis Cup in 1995. The year should be considered the peak of the rivalry as together they won three out of four major titles, meeting each other twice in the finals, and were occupying the top two spots in the rankings for the whole year. They met five times during the year, all in the title matches, including the Australian Open, the Newsweek Champions Cup (now Indian Wells), the Lipton International Players Championships (now Miami Open), the Canadian Open, and the US Open. Agassi won three of the finals, including the Australian Open; however, Sampras took the US Open title, ending Agassi's 26-match winning streak. After Agassi had taken most of the fall season off, Sampras took over the No. 1 ranking for the end of the season. Agassi admitted this loss, which gave Sampras a 9–8 lead in their head-to-head meetings, took two years for him to get over it mentally.

In the following three years, while Sampras continued winning Grand Slam titles every season, Agassi slumped in the rankings and struggled in major competitions. The next time Sampras and Agassi met in a Grand Slam final was at Wimbledon in 1999, where Sampras won in straight sets. For both, it was considered a career rejuvenation, as Sampras had suffered a string of disappointments in the previous year while Agassi was regaining his status as a top-ranked player after winning the French Open. Sampras forfeited the No. 1 ranking to Agassi when injury forced him to withdraw from that year's US Open, which Agassi went on to win. They faced each other twice in the season-ending ATP Tour World Championships, with Sampras losing the round-robin match, but winning the final.

In the 2000s, they met three more times on the Grand Slam level offering three memorable contests. In 2000, the top-ranked Agassi defeated No. 3 Sampras in the semi-finals of the Australian Open in five sets, which was an important win for Agassi who had lost 4 of the previous five matches against Sampras. In arguably their most memorable match ever, Sampras defeated Agassi in the 2001 US Open quarterfinals in four sets. There were no breaks of serve during the entire match. Reruns of the match are frequently featured on television, especially during US Open rain delays, and the match is considered one of the best in history because of the level of play presented by both players.

Their last meeting was the final of the 2002 US Open, which was their third meeting in a US Open final, but the first since 1995. The match was also notable because they had defeated several up-and-coming players en route to the final. Sampras had defeated No. 3 Tommy Haas in the fourth round and future No. 1 Andy Roddick in the quarterfinals, while Agassi had defeated No. 1 and defending champion Lleyton Hewitt in the semi-finals. Sampras defeated Agassi in four sets. This was the final ATP tour singles match of Sampras's career.

Agassi vs. Chang

Michael Chang was the opponent Agassi faced most frequently from all the players other than Sampras. They met 22 times on the tour level with Agassi leading 15–7. Chang, unlike most of Agassi's big rivals, had a playing style similar to his. Both players preferred to stay at the baseline with Chang being more defensive-minded. The outcome was that most of their meetings were built on long and entertaining rallies. The rivalry began late in the 1980s with both players being considered the prodigies of the next great generation of American tennis players and both being of foreign descent.

Agassi won the first four matches including a straight-set victory in round 16 of the 1988 US Open and defeating Chang, the defending champion, in the 1990 French Open in a four-set quarterfinal. Arguably their best match took place in the round of 16 of the 1994 US Open. While both players presented high-quality shot-making, the momentum changed from set to set with Agassi eventually prevailing in a five-set victory. It turned out to be the toughest contest on his way to his first US Open title. Their next two Grand Slam meetings came in 1996, with Chang recording easy straight-set victories in the semi-finals of both the Australian Open and the US Open. Years after, Agassi shockingly admitted in his book that he had lost the first of the matches on purpose as he did not want to face Boris Becker, who was awaiting the winner in the final. Agassi won the last four of their matches, with the last being in 2003 at the Miami Open with Chang being clearly past his prime.

Agassi vs. Becker

Boris Becker and Agassi played 14 times with Agassi leading 10–4. Becker won their first three matches in 1988 and 1989 before Agassi reversed the rivalry in 1990, and won 10 of their last 11 matches. They first played at Indian Wells in 1988, with Becker prevailing. Their most notable match was the 1989 Davis Cup semi-final match, which Becker won in five sets after losing the first two in tiebreaks. Agassi, considered a baseliner with a playing style not suiting grass, shocked Becker, a three-time champion, in a five-set quarterfinal at Wimbledon in 1992 on his way to his first Grand Slam title. The intensity of the rivalry peaked in 1995. Becker won that year's Wimbledon semi-final after being down a set and two breaks, to eventually win in four sets. In a highly anticipated rematch in the US Open semi-final, this time it was Agassi who came out victorious in four tight sets. Their final match was played at Hong Kong in 1999, which Agassi won in three sets.

Agassi vs. Rafter

Agassi and Pat Rafter played fifteen times with Agassi leading 10–5. The rivalry has been considered special and delivered memorable encounters, because of the players' contrasting styles of play, with Rafter using traditional serve-&-volley methods against Agassi's variety of return of serves and passing shots as his main weapons. Agassi led 8–2 on hard courts, but Rafter surprisingly won their sole match on clay at the 1999 Rome Masters. They played four matches at Wimbledon with both winning two matches each. Agassi won the first two in 1993 and 1999, while Rafter took their 2000 and 2001 encounters, the latter two matches being gruelling 5-setters often being presented on the lists of best matches ever played. Agassi also won both their meetings at the Australian Open, in 1995 and 2001, on his way to the title on both occasions. Rafter, however, took their only US Open encounter in 1997 and went on to win the title.

Agassi vs. Federer

Agassi and Roger Federer played 11 times, and Federer led their head-to-head series 8–3. With the retirement of Sampras, the rivalry against the 11-years-younger Federer, who was another great server like Sampras, became Agassi's main rivalry for the final years of his career. Agassi won their first three matches, but then went on to lose eight consecutive ones. They first met in just the third tournament of Federer's career at the 1998 Swiss Indoors in Federer's hometown, with Agassi prevailing over the 17-year-old. Agassi also defeated Federer at the 2001 US Open and the finals of the Miami Open in 2002. Federer began to turn the tide at the Masters Cup in 2003, when he defeated Agassi in both the round-robin and the final. They played a memorable quarterfinal match at the 2004 US Open that spanned over two windy days, with Federer eventually prevailing in five sets. At the 2005 Dubai Championships, Federer and Agassi attracted worldwide headlines with a publicity stunt that saw the two tennis legends play on a helipad almost 220 meters above sea level at the hotel Burj al-Arab. Their final duel took place in the final of the 2005 US Open. In the historic clash of generations, Federer was victorious in four sets in front of a pro-Agassi crowd. The match was the last appearance by Agassi in any tournament final.

Agassi vs. Lendl

Agassi and Ivan Lendl played eight times, and Lendl led their head-to-head series 6–2.

Agassi vs. Edberg

Agassi and Stefan Edberg played nine times, and Agassi led their head-to-head series 6–3.

Earnings

Agassi earned more than $30 million in prize-money during his career, sixth only to Djokovic, Federer, Nadal, Sampras and Murray to date (May 2018). He also earned more than $25 million a year through endorsements during his career, which was ranked fourth in all sports at the time.

Post-retirement

Since retiring after the 2006 US Open, Agassi has participated in a series of charity tournaments and continues his work with his own charity. On September 5, 2007, he was a surprise guest commentator for the Andy Roddick/ Roger Federer US Open quarterfinal. He played an exhibition match at Wimbledon, teaming with his wife, Steffi Graf, to play with Tim Henman and Kim Clijsters. He played World Team Tennis for the Philadelphia Freedoms in the summer of 2009. At the 2009 French Open, Agassi was on hand to present Roger Federer, who completed his Career Grand Slam by winning the tournament and joined Agassi as one of six men to complete the Career Grand Slam, with the trophy.

Also in 2009, Agassi played at the Outback Champions Series event for the first time. He played the Cancer Treatment Centers of America Tennis Championships at Surprise, Arizona, where he reached the final before bowing to eventual champion Todd Martin. Agassi returned to the tour renamed for the PowerShares Series in 2011 and participated in a total of seven events while winning two. Agassi beat Courier in the final of the Staples Champions Cup in Boston and later defeated Sampras at the CTCA Championships at his hometown Las Vegas.

In 2012, Agassi took part in five tournaments, winning three of those. In November, at first he won BILT Champions Showdown in San Jose, beating John McEnroe in the final. The following day, he defended his title of the CTCA Championships, while defeating Courier in the decisive match. In the series season finale, he beat Michael Chang for the Acura Champions Cup. The series and Agassi came back to action in 2014. Agassi won both tournaments he participated in. At the Camden Wealth Advisors Cup's final in Houston, Agassi beat James Blake for a rematch of their 2005 US Open quarterfinal. He defeated Blake again in Portland to win the title of the Cancer Treatment Centers of America Championships. In 2015, Agassi took part in just one event of the PowerShares Series, losing to Mark Philippoussis in the final of the Champions Shootout. The following year he took part in two events, at first losing to Blake in Chicago, and the next day defeating Mardy Fish, but losing to Roddick in Charleston.

In 2009, in Macau Agassi and Sampras met for the first time on court since the 2002 US Open final. Sampras won the exhibition in three sets. The rivalry between the former champions headlined sports media again in March 2010 after the two participated in the "Hit for Haiti" charity event organized to raise money for the victims of the earthquake. Partnered with Roger Federer and Rafael Nadal, the old rivals began making jokes at each other's expense, which ended up with Sampras intentionally striking a serve at Agassi's body. After the event, Agassi admitted that he had crossed the line with his jokes and publicly apologized to Sampras. Agassi and Sampras met again one year later for an exhibition match at Madison Square Garden in New York in front of 19 000 spectators as Sampras defeated Agassi in two sets. On March 3, 2014, Agassi and Sampras squared off for an exhibition in London for the annual World Tennis Day. This time, it was Agassi who came out on top in two straight sets.

He returned to the tour in May 2017 in the position of coach to Novak Djokovic for the French Open. Agassi announced the end of the partnership on March 31, 2018, stating that there were too many disagreements in the relationship.

Playing style

Early in his career, Agassi would look to end points quickly by playing first-strike tennis, typically by inducing a weak return with a deep, hard shot, and then playing a winner at an extreme angle. On the rare occasion that he charged the net, Agassi liked to take the ball in the air and hit a swinging volley for a winner. His favored groundstroke was his flat, accurate two-handed backhand, hit well cross-court but especially down the line. His forehand was nearly as strong, especially his inside-out to the ad court.

Agassi's strength was in dictating play from the baseline, and he was able to consistently take the ball on the rise. While he was growing up, his father and Nick Bollettieri trained him in this way.Open: Andre Agassi HarpersCollins 2009 When in control of a point, Agassi would often pass up an opportunity to attempt a winner and hit a conservative shot to minimize his errors, and to make his opponent run more. This change to more methodical, less aggressive baseline play was largely initiated by his longtime coach, Brad Gilbert, in their first year together in 1994. Gilbert encouraged Agassi to wear out opponents with his deep, flat groundstrokes and to use his fitness to win attrition wars, and noted Agassi's two-handed backhand down the line as his very best shot. A signature play later in his career was a change-up drop shot to the deuce court after deep penetrating groundstrokes. This would often be followed by a passing shot or lob if the opponent was fast enough to retrieve it.

Agassi was raised on hardcourts, but found much of his early major-tournament success on the red clay of Roland Garros, reaching two consecutive finals there early in his career. Despite grass being his worst surface, his first major win was at the slick grass of Wimbledon in 1992, a tournament that he professed to hating at the time. His strongest surface over the course of his career, was indeed hardcourt, where he won six of his eight majors.

Business ventures

Agassi established a limited liability company named Andre Agassi Ventures (formerly named Agassi Enterprises). Agassi, along with five athlete partners (including Wayne Gretzky, Joe Montana, Shaquille O'Neal, Ken Griffey Jr., and Monica Seles) opened a chain of sports-themed restaurant named Official All Star Café in April 1996. The restaurant closed down in 2001.

In 1999, he paid $1 million for a 10 percent stake in Nevada First Bank and made a $10 million profit when it was sold to Western Alliance Bancorp in 2006.

In 2002, he joined the Tennis Channel to promote the channel to consumers and cable and satellite industry, and made an equity investment in the network. After meeting chef Michael Mina at one of his restaurants in San Francisco, Agassi partnered with him in 2002 to start Mina Group Inc. and opened 18 concept restaurants in San Francisco, San Jose, Dana Point, Atlantic City and Las Vegas. Agassi was an equity investor of a group that acquired Golden Nugget Las Vegas and Golden Nugget Laughlin from MGM Mirage for $215 million in 2004. One year later, the group sold the hotel-casino to Landry's, Inc. for $163 million in cash and $182 million in assumed debt. In 2007, he sat on the board of Meadows Bank, an independent bank in Nevada. He has invested in start-up companies backed by Allen & Company.

Agassi and Graf formed a company called Agassi Graf Holdings. They invested in PURE, a nightclub at Caesars Palace, which opened in 2004, and sold it to Angel Management Group in 2010. In August 2006, Agassi and Graf developed a joint venture with high-end furniture maker Kreiss Enterprises. They launched a furniture line called Agassi Graf Collection. In September, Agassi and Graf, through their company Agassi Graf Development LLC, along with Bayview Financial LP, finalized an agreement to develop a condominium hotel, Fairmont Tamarack, at Tamarack Resort in Donnelly, Idaho

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