The Order of Merit was won by Scotland's Colin Montgomerie.
The table below shows the 1999 European Tour schedule which was made up of 42 regular tournaments, which included the four major championships and the major national opens around Europe. There were several changes from the previous season, with the addition of three World Golf Championships, the Malaysian Open, the Estoril Open, the West of Ireland Golf Classic, the Scottish PGA Championship and the Sarazen World Open, and the loss of the Johnnie Walker Classic due to rescheduling from January to November, the Cannes Open and the Open Novotel Perrier. Money earned from the U.S. Open, PGA Championship and World Golf Championships counted towards the Order of Merit.
The numbers in parentheses after the winners' names show the number of career wins they had on the European Tour up to and including that event. This is only shown for members of the European Tour.
|14–17 Jan||Alfred Dunhill South African PGA Championship||South Africa||Ernie Els (7)|
|21–24 Jan||Mercedes-Benz - Vodacom South African Open||South Africa||David Frost (2)|
|28–31 Jan||Heineken Classic||Australia||Jarrod Moseley (1)|
|4–7 Feb||Benson and Hedges Malaysian Open||Malaysia||Gerry Norquist (1)||New tournament|
|11–14 Feb||Dubai Desert Classic||United Arab Emirates||David Howell (1)|
|17–20 Feb||Qatar Masters||Qatar||Paul Lawrie (2)|
|24–28 Feb||WGC-Andersen Consulting Match Play Championship||United States||Jeff Maggert (n/a)|
|4–7 Mar||Algarve Portuguese Open||Portugal||Van Phillips (1)|
|11–14 Mar||Turespana Masters - Open Andalucia||Spain||Miguel Ángel Jiménez (5)|
|25–28 Mar||Madeira Island Open||Portugal||Pedro Linhart (1)|
|8–11 Apr||Masters Tournament||United States||José María Olazábal (19)||Unofficial money|
|15–18 Apr||Estoril Open||Portugal||Jean-François Remésy (1)||New tournament|
|22–25 Apr||Peugeot Open de Espana||Spain||Jarmo Sandelin (3)|
|29 Apr – 2 May||Fiat and Fila Italian Open||Italy||Dean Robertson (1)|
|6–9 May||Novotel Perrier Open de France||France||Retief Goosen (3)|
|13–16 May||Benson and Hedges International Open||England||Colin Montgomerie (18)|
|21–24 May||Deutsche Bank - SAP Open TPC of Europe||Germany||Tiger Woods (n/a)|
|28–31 May||Volvo PGA Championship||England||Colin Montgomerie (19)|
|3–6 Jun||Compass Group English Open||England||Darren Clarke (5)|
|10–13 Jun||German Open||Germany||Jarmo Sandelin (4)|
|17–20 Jun||Moroccan Open||Morocco||Miguel Ángel Martín (3)|
|17–20 Jun||U.S. Open||United States||Payne Stewart (n/a)|
|24–27 Jun||Compaq European Grand Prix||England||David Park (1)|
|1–4 Jul||Murphy's Irish Open||Republic of Ireland||Sergio García (1)|
|8–11 Jul||Standard Life Loch Lomond||Scotland||Colin Montgomerie (20)|
|15–18 Jul||The Open Championship||Scotland||Paul Lawrie (3)|
|22–25 Jul||TNT Dutch Open||Netherlands||Lee Westwood (7)|
|30 Jul – 2 Aug||Smurfit European Open||Republic of Ireland||Lee Westwood (8)|
|5–8 Aug||Volvo Scandinavian Masters||Sweden||Colin Montgomerie (21)|
|12–15 Aug||PGA Championship||United States||Tiger Woods (n/a)|
|12–15 Aug||West of Ireland Golf Classic||Republic of Ireland||Costantino Rocca (5)||New tournament.
Alternate to PGA Championship
|19–22 Aug||BMW International Open||Germany||Colin Montgomerie (22)|
|26–29 Aug||WGC-NEC Invitational||United States||Tiger Woods (n/a)|
|27–30 Aug||Scottish PGA Championship||Scotland||Warren Bennett (1)||New tournament.
Alternate to WGC
|2–5 Sep||Canon European Masters||Switzerland||Lee Westwood (9)|
|9–12 Sep||Victor Chandler British Masters||England||Bob May (1)|
|16–19 Sep||Trophée Lancôme||France||Pierre Fulke (1)|
|24–27 Sep||Ryder Cup||United States||United States||Team event|
|30 Sep – 3 Oct||Linde German Masters||Germany||Sergio García (2)|
|7–10 Oct||Alfred Dunhill Cup||Scotland||Spain||Team event.
|14–17 Oct||Cisco World Match Play Championship||England||Colin Montgomerie (n/a)||Unofficial money|
|14–17 Oct||Sarazen World Open||Spain||Thomas Bjørn (4)||New tournament|
|21–24 Oct||Belgacom Open||Belgium||Robert Karlsson (3)|
|28–31 Oct||Volvo Masters||Spain||Miguel Ángel Jiménez (6)|
|4–7 Nov||WGC-American Express Championship||Spain||Tiger Woods (n/a)|
|18–21 Nov||World Cup of Golf||Malaysia||United States||Team event.
|Position||Player||Country||Prize money (€)|
|4||Miguel Ángel Jiménez||Spain||1,148,290|
|5||Retief Goosen||South Africa||1,059,985|
|8||Darren Clarke||Northern Ireland||731,291|