2020–21 Dundee F.C. Season

The 2020–21 season was Dundee's second season in the second tier of Scottish football since their relegation at the end of the 2018–19 season.

Due to the disruption caused by the COVID-19 pandemic, the teams in the Scottish Championship agreed to shorten the season to 27 games rather than the regular 36, with a start date on 17 October 2020.
Dundee will also compete in the League Cup and the Scottish Cup, but the tournament was cancelled due to the financial strain of the ongoing pandemic.

Dundee would earn promotion after winning the Premiership play-offs, defeating both Raith Rovers and Kilmarnock over two legs to return to the Scottish Premiership after a two-year absence.

Season summary

Pre-season

In the wake of the uncertainty brought on by the COVID-19 pandemic, Dundee would furlough its players and staff, but ensure they would receive their usual salaries. The financial strain caused by the pandemic led to the club needing to cut costs, initially confirming the departure of assistant manager Jimmy Nicholl and asking the players to take wage cuts of up to 30 per cent in June 2020. After discussions lasting several weeks, 12 of the 13 players asked to take cuts agreed, with striker Kane Hemmings the only one to hold out longer. Despite initially agreeing to the wage cut as well, Hemmings decided to renege and leave the club in August. Later that month, Dundee would make cuts to their Youth Academy coaching staff, though the majority of coaches would continue their roles in a voluntary capacity. The club would also appoint former player and first-team coach Dave Mackay as assistant manager.

Dundee would bring in several new players, most notably Dundee-born and ex-Premier League player Charlie Adam, who supported the club as a boy and described signing for the club as a "dream".

October

Dundee were set to play their first competitive game of the season in the League Cup at home to Forfar Athletic, but the game was called off and Dundee were awarded a 3–0 win by the SPFL following a Forfar player testing positive for COVID-19. They would begin their competitive campaign four days later, in an away win to Highland League champions Brora Rangers. The following week, Dundee would play their first league game of the season away to the recently relegated Heart of Midlothian in a highly anticipated opening game, described by the media as a 'grudge match' after the voting fiasco which marred the end of the previous season, in which a controversial Dundee vote ended the season in March and would lead to Hearts' relegation. In a turbulent game, Dundee would be completely outmatched in a 6–2 thrashing at Tynecastle. After this evisceration, Dundee would pick themselves up and get a much-needed win the following week at home to Greenock Morton, with loanee Jonathan Afolabi scoring his first competitive goal for the club in the 1–0 win. The ''Dark Blues'' looked set to repeat this result the following week against newly-promoted Raith Rovers through Charlie Adam's strike, but a late equaliser denied them from taking another 3 points.

November

Dundee would again struggle away from home, needing inspiration from Adam to score two late goals against part-time Alloa Athletic in order to escape Recreation Park with a point in a wild 3–3 draw. Two days later, midfielder Graham Dorrans would leave the side and move to Australia to play with Western Sydney Wanderers. Returning to League Cup action, Dundee would win comfortably against Scottish League One side Cove Rangers. Despite equalling high-flying Premiership side Hibernian for most of their final group stage game, a late flurry from the ''Hibees'' would result in a heavy 4–1 defeat, though Dundee would still qualify for the following round of the cup. Dundee would coincidentally have to play Hibs away once again after drawing them in the next round. Before that, Dundee would return to league action, but would severely disappoint with an awful start in a defeat at Somerset Park against Ayr United. In their League Cup rematch against Hibs at Easter Road, Dundee would fall to their third consecutive defeat in a close 1–0 loss that would knock them out.

December

In their first home league game in over a month, Dundee would return to winning ways with another tight 1–0 victory against Arbroath through a Paul McGowan solo goal. In a back-and-forth affair at Caledonian Stadium the following week, they would earn a point through a late Jordan McGhee equaliser. Dundee looked to have swept past high-flying league rivals Dunfermline Athletic with a dominant 3–0 lead late on, but a quick collapse allowed the ''Pars'' to snatch an unlikely point at Dens Park. Despite the prior week's disappointment, the side put it aside and would record a comfortable Boxing Day win away to Queen of the South through an Osman Sow hat-trick. The Dee would record another three goals and a win three days later at home to Alloa, with Sow scoring a brace to make it 6 goals for him in 3 games and bringing them up to third place in the league.

January

Dundee would gain a measure of revenge over their opening day humiliation against Hearts with a commanding 3–1 win at Dens, scoring 3 goals in 4 consecutive games for the first time in 43 years. They would follow up this impressive performance with a much less impressive one, needing a last-minute equaliser and another comeback in extra time to defeat Lowland League side Bonnyrigg Rose Athletic in the Scottish Cup