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| 1st(1st leg) | Udinese Calcio | - | Bayer Leverkusen | 0:1 (0:0) | ||
| 2nd (2nd leg) | Bayer Leverkusen | - | Udinese Calcio | 1:2 (1:2) | ||
| 1st(1st leg): 23/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Udinese Calcio | ||||
| 1st(1st leg) | AEK Athen | - | AS Monaco | 2:2 (1:1) | ||
| 2nd (2nd leg) | AS Monaco | - | AEK Athen | 1:0 (1:0) | ||
| 1st(1st leg): 23/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: AS Monaco | ||||
| 1st(1st leg) | Bologna FC | - | Galatasaray | 1:1 (0:0) | ||
| 2nd (2nd leg) | Galatasaray | - | Bologna FC | 2:1 (2:1) | ||
| 1st(1st leg): 23/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Galatasaray | ||||
| 1st(1st leg) | VfL Wolfsburg | - | Atlético Madrid | 2:3 (1:2) | ||
| 2nd (2nd leg) | Atlético Madrid | - | VfL Wolfsburg | 2:1 (1:0) | ||
| 1st(1st leg): 23/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Atlético Madrid | ||||
| 1st(1st leg) | Slavia Praha | - | AFC Steaua București | 4:1 (2:0) | ||
| 2nd (2nd leg) | AFC Steaua București | - | Slavia Praha | 1:1 (1:0) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Slavia Praha | ||||
| 1st(1st leg) | Parma AC | - | Sturm Graz | 2:1 (1:1) | ||
| 2nd (2nd leg) | Sturm Graz | - | Parma AC | 3:3 (0:1, 2:1) aet | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Parma AC | ||||
| 1st(1st leg) | RC Lens | - | 1. FC Kaiserslautern | 1:2 (0:2) | ||
| 2nd (2nd leg) | 1. FC Kaiserslautern | - | RC Lens | 1:4 (1:2) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: RC Lens | ||||
| 1st(1st leg) | Olympiakos Piraeus | - | Juventus | 1:3 (1:1) | ||
| 2nd (2nd leg) | Juventus | - | Olympiakos Piraeus | 1:2 (1:1) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 07/12/1999 | Winner: Juventus | ||||
| 1st(1st leg) | Olympique Lyon | - | Werder Bremen | 3:0 (2:0) | ||
| 2nd (2nd leg) | Werder Bremen | - | Olympique Lyon | 4:0 (2:0) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 07/12/1999 | Winner: Werder Bremen | ||||
| 1st(1st leg) | AFC Ajax | - | RCD Mallorca | 0:1 (0:1) | ||
| 2nd (2nd leg) | RCD Mallorca | - | AFC Ajax | 2:0 (1:0) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: RCD Mallorca | ||||
| 1st(1st leg) | Arsenal FC | - | FC Nantes | 3:0 (1:0) | ||
| 2nd (2nd leg) | FC Nantes | - | Arsenal FC | 3:3 (1:3) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Arsenal FC | ||||
| 1st(1st leg) | Deportivo La Coruña | - | Panathinaikos | 4:2 (4:1) | ||
| 2nd (2nd leg) | Panathinaikos | - | Deportivo La Coruña | 1:1 (0:0) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Deportivo La Coruña | ||||
| 1st(1st leg) | AS Roma | - | Newcastle United | 1:0 (0:0) | ||
| 2nd (2nd leg) | Newcastle United | - | AS Roma | 0:0 (0:0) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: AS Roma | ||||
| 1st(1st leg) | RC Celta | - | SL Benfica | 7:0 (4:0) | ||
| 2nd (2nd leg) | SL Benfica | - | RC Celta | 1:1 (0:1) | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 09/12/1999 | Winner: RC Celta | ||||
| 1st(1st leg) | Rangers FC | - | Borussia Dortmund | 2:0 (2:0) | ||
| 2nd (2nd leg) | Borussia Dortmund | - | Rangers FC | 3:1 (1:0, 2:0, 2:0) pso | ||
| 1st(1st leg): 25/11/1999 | 2nd (2nd leg): 07/12/1999 | Winner: Borussia Dortmund | ||||
| 1st(1st leg) | Spartak Moskva | - | Leeds United | 2:1 (1:1) | ||
| 2nd (2nd leg) | Leeds United | - | Spartak Moskva | 1:0 (0:0) | ||
| 1st(1st leg): 02/12/1999 | 2nd (2nd leg): 09/12/1999 | Winner: Leeds United | ||||
