| Tourney Name: | UEFA Champions League |
| Year: | 1999–2000 |
| Dates: | Qualifying: 13 July – 25 August 1999 Competition proper: 14 September 1999 – 24 May 2000 |
| Num Teams: | Competition proper: 32 Total: 71 |
| Champion Other: |  Real Madrid |
| Count: | 8 |
| Second Other: | Valencia |
| Matches: | 157 |
| Goals: | 442 |
| Attendance: | 5495112 |
| Top Scorer: | Raúl (Real Madrid) Rivaldo (Barcelona) Mário Jardel (Porto) 10 goals each |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
The 1999–2000 UEFA Champions League was the 45th season of the UEFA Champions League, UEFA's premier European club football tournament, and the eighth season since its rebranding from the "European Champion Clubs' Cup" or "European Cup". The competition was won by Real Madrid, who clinched a historic eighth title win by beating fellow La Liga side, Valencia in the final. The final was hosted in the Stade de France in Paris, the city where the original roots of the competition had begun nearly 50 years earlier.
Just after two years of allowing runners-up of strongest continental leagues to enter the tournament, UEFA went even further and expanded the tournament to up to four strongest teams from Europe's top national leagues. As a result, the tournament was a stark contrast from 1996–97 (which took place only three years prior) where only top national champions and title holders participated.
The competition was dominated by the Spanish teams, with three of the four semi-finalists coming from Spain, namely Real Madrid, Valencia and Barcelona. The final between Real Madrid and Valencia marked the first time that both finalists in the competition had come from the same country.
Manchester United were the defending champions, but were eliminated by eventual winners Real Madrid in the quarter-finals.
The 1999–2000 edition of the Champions League featured a whole different format to the competition. An additional qualifying round was introduced to generate two group stages, firstly with 32 teams – eight groups of four – who played six matches each to reduce the competition to 16 teams for the second group stage, with the eight third-placed teams moving to the UEFA Cup third round. At the end of the second group stage, eight teams remained to contest the knock-out stage.[1]
A total of 71 teams participated in the 1999–2000 Champions League, from 47 of 51 UEFA associations. Liechtenstein (who don't have their own league) as well as Andorra and San Marino did not participate. Additionally, Bosnia and Herzegovina were not admitted due to having no nation-wide champion.
Below is the qualification scheme for the 2000–01 UEFA Champions League:[2]
Countries are allocated places according to their 1998 UEFA league coefficient, which takes into account their performance in European competitions from 1993–94 to 1997–98.[3]
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The title holders (Manchester United) qualified for the Champions League group stage through their domestic league, thus the group stage spot reserved for the title holders was vacated. Additionally, Bosnia and Herzegovina was not admitted as their play-off for Champions League qualification didn't take place. Due to these factors, the following changes to the default access list are made:
| Teams entering this round | Teams advancing from previous round | |||
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| First qualifying round (18 teams) |
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| Second qualifying round (28 teams) |
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| Third qualifying round (32 teams) |
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| First group stage (32 teams) |
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| Second group stage (16 teams) |
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| Knockout phase (8 teams) |
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League positions of the previous season shown in parentheses (TH: Champions League title holders).
The schedule of the competition is as follows (all draws are held in Geneva, Switzerland, unless stated otherwise).[4]
| Phase | Round | Draw date | First leg | Second leg |
|---|---|---|---|---|
| Qualifying | First qualifying round | 30 June 1999 | 13–14 July 1999 | 21 July 1999 |
| Second qualifying round | 28 July 1999 | 4 August 1999 | ||
| Third qualifying round | 23 July 1999 | 10–11 August 1999 | 25 August 1999 | |
| First group stage | Matchday 1 | 26 August 1999 (Monaco) | 14–15 September 1999 | |
| Matchday 2 | 21–22 September 1999 | |||
| Matchday 3 | 28–29 September 1999 | |||
| Matchday 4 | 19–20 October 1999 | |||
| Matchday 5 | 26–27 October 1999 | |||
| Matchday 6 | 2–3 November 1999 | |||
| Second group stage | Matchday 1 | 5 November 1999 | 23–24 November 1999 | |
| Matchday 2 | 7–8 December 1999 | |||
| Matchday 3 | 29 February – 1 March 2000 | |||
| Matchday 4 | 7–8 March 2000 | |||
| Matchday 5 | 14–15 March 2000 | |||
| Matchday 6 | 21–22 March 2000 | |||
| Knockout phase | Quarter-finals | 24 March 2000 | 4–5 April 2000 | 18–19 April 2000 |
| Semi-finals | 2–3 May 2000 | 9–10 May 2000 | ||
| Final | 24 May 2000 at Stade de France, Saint-Denis | |||
See main article: 1999–2000 UEFA Champions League qualifying rounds.
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Losing teams advanced to the first round of the 1999–2000 UEFA Cup.
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See main article: 1999–2000 UEFA Champions League first group stage.
16 winners from the third qualifying round, 10 champions from countries ranked 1–10, and six second-placed teams from countries ranked 1–6 were drawn into eight groups of four teams each. Compared to the two previous seasons, three associations (England, France, The Netherlands) were allowed three teams – the league winner and runner-up from each nation qualified for the first group stage, and the third-placed teams qualified for the third qualifying round – and three associations were allowed four teams (Germany, Italy, Spain) – the league winner and runner-up from each nation qualified for the first group stage, and the third- and fourth-placed teams qualified for the third qualifying round. Nine additional associations were still allowed two teams (Czech Republic, Greece, Norway, Portugal: league winner in group stage; Austria, Croatia, Denmark, Turkey, Russia: league winner in third qualifying round). The top two teams in each group advanced to the Champions League second group stage, while the third-placed teams advanced to round three of the UEFA Cup.
AIK, Boavista, Bordeaux, Chelsea, Fiorentina, Hertha BSC, Lazio, Maribor, Molde, Valencia and Willem II made their debut in the group stage. Maribor was the first Slovenian side to play in group stage. Germany became the first association to have four teams in the Champions League group stage.
Tiebreakers, if necessary, are applied in the following order:
See main article: 1999–2000 UEFA Champions League second group stage.
Eight winners and eight runners-up from the first group stage were drawn into four groups of four teams each, each containing two group winners and two runners-up. Teams from the same country or from the same first-round group could not be drawn together. The top two teams in each group advanced to the quarter-finals.
See main article: 1999–2000 UEFA Champions League knockout stage.
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See main article: 2000 UEFA Champions League final.
The top scorers from the 1999–2000 UEFA Champions League (excluding qualifying rounds) are as follows:
| Rank | Name | Team | Goals | Minutes played |
|---|---|---|---|---|
| 1 |  Mário Jardel | Porto | 10 | 1150 |
| Rivaldo | Barcelona | 10 | 1229 | |
| Raúl | Real Madrid | 10 | 1350 | |
| 4 |  Simone Inzaghi | Lazio | 9 | 700 |
| 5 |  Serhiy Rebrov | Dynamo Kyiv | 8 | 1061 |
 Tore André Flo | Chelsea | 8 | 1159 | |
| 7 | Paulo Sérgio | Bayern Munich | 7 | 1007 |
| Patrick Kluivert | Barcelona | 7 | 1203 | |
| 9 | Luis Enrique | Barcelona | 6 | 581 |
 Gabriel Batistuta | Fiorentina | 6 | 875 | |
| Roy Keane | Manchester United | 6 | 1048 | |
| Fernando Morientes | Real Madrid | 6 | 1129 |
