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| 1st(1st leg) | Aris Saloniki | - | RC Celta | 2:2 (1:2) | ||
| 2nd (2nd leg) | RC Celta | - | Aris Saloniki | 2:0 (0:0) | ||
| 1st(1st leg): 19/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: RC Celta | ||||
| 1st(1st leg) | Udinese Calcio | - | Legia Warszawa | 1:0 (1:0) | ||
| 2nd (2nd leg) | Legia Warszawa | - | Udinese Calcio | 1:1 (1:1) | ||
| 1st(1st leg): 19/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Udinese Calcio | ||||
| 1st(1st leg) | Deportivo La Coruña | - | Montpellier HSC | 3:1 (1:1) | ||
| 2nd (2nd leg) | Montpellier HSC | - | Deportivo La Coruña | 0:2 (0:1) | ||
| 1st(1st leg): 19/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Deportivo La Coruña | ||||
| 1st(1st leg) | Slavia Praha | - | Grasshopper Club Zürich | 3:1 (2:1) | ||
| 2nd (2nd leg) | Grasshopper Club Zürich | - | Slavia Praha | 1:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Slavia Praha | ||||
| 1st(1st leg) | FK AŠK Inter Slovnaft Bratislava | - | FC Nantes | 0:3 (0:2) | ||
| 2nd (2nd leg) | FC Nantes | - | FK AŠK Inter Slovnaft Bratislava | 4:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: FC Nantes | ||||
| 1st(1st leg) | Widzew Łódź | - | AS Monaco | 1:1 (1:1) | ||
| 2nd (2nd leg) | AS Monaco | - | Widzew Łódź | 2:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 02/11/1999 | Winner: AS Monaco | ||||
| 1st(1st leg) | Levski Sofia | - | Juventus | 1:3 (0:1) | ||
| 2nd (2nd leg) | Juventus | - | Levski Sofia | 1:1 (0:1) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Juventus | ||||
| 1st(1st leg) | Werder Bremen | - | Viking FK | 0:0 (0:0) | ||
| 2nd (2nd leg) | Viking FK | - | Werder Bremen | 2:2 (1:1) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Werder Bremen | ||||
| 1st(1st leg) | IFK Göteborg | - | AS Roma | 0:2 (0:1) | ||
| 2nd (2nd leg) | AS Roma | - | IFK Göteborg | 1:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: AS Roma | ||||
| 1st(1st leg) | FK Teplice | - | RCD Mallorca | 1:2 (0:2) | ||
| 2nd (2nd leg) | RCD Mallorca | - | FK Teplice | 3:0 (1:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: RCD Mallorca | ||||
| 1st(1st leg) | AFC Steaua București | - | West Ham United | 2:0 (1:0) | ||
| 2nd (2nd leg) | West Ham United | - | AFC Steaua București | 0:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: AFC Steaua București | ||||
| 1st(1st leg) | Hapoel Haifa | - | AFC Ajax | 0:3 (0:2) | ||
| 2nd (2nd leg) | AFC Ajax | - | Hapoel Haifa | 0:1 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: AFC Ajax | ||||
| 1st(1st leg) | MTK Hungaria | - | AEK Athen | 2:1 (2:0) | ||
| 2nd (2nd leg) | AEK Athen | - | MTK Hungaria | 1:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 02/11/1999 | Winner: AEK Athen | ||||
| 1st(1st leg) | PAOK Saloniki | - | SL Benfica | 1:2 (0:0) | ||
| 2nd (2nd leg) | SL Benfica | - | PAOK Saloniki | 4:1 (1:2, 1:2, 1:2) pso | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: SL Benfica | ||||
| 1st(1st leg) | RSC Anderlecht | - | Bologna FC | 2:1 (2:0) | ||
| 2nd (2nd leg) | Bologna FC | - | RSC Anderlecht | 3:0 (1:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 02/11/1999 | Winner: Bologna FC | ||||
| 1st(1st leg) | FC Zürich | - | Newcastle United | 1:2 (0:0) | ||
| 2nd (2nd leg) | Newcastle United | - | FC Zürich | 3:1 (1:1) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Newcastle United | ||||
| 1st(1st leg) | Grazer AK | - | Panathinaikos | 2:1 (0:0) | ||
| 2nd (2nd leg) | Panathinaikos | - | Grazer AK | 1:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Panathinaikos | ||||
| 1st(1st leg) | Roda JC Kerkrade | - | VfL Wolfsburg | 0:0 (0:0) | ||
| 2nd (2nd leg) | VfL Wolfsburg | - | Roda JC Kerkrade | 1:0 (0:0) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 02/11/1999 | Winner: VfL Wolfsburg | ||||
| 1st(1st leg) | Olympique Lyonnais | - | Celtic FC | 1:0 (0:0) | ||
| 2nd (2nd leg) | Celtic FC | - | Olympique Lyonnais | 0:1 (0:1) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Olympique Lyonnais | ||||
| 1st(1st leg) | Leeds United | - | Lokomotiv Moskva | 4:1 (2:0) | ||
| 2nd (2nd leg) | Lokomotiv Moskva | - | Leeds United | 0:3 (0:3) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Leeds United | ||||
| 1st(1st leg) | Parma AC | - | Helsingborgs IF | 1:0 (1:0) | ||
| 2nd (2nd leg) | Helsingborgs IF | - | Parma AC | 1:3 (0:3) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Parma AC | ||||
| 1st(1st leg) | Atlético Madrid | - | Amica Wronki | 1:0 (0:0) | ||
| 2nd (2nd leg) | Amica Wronki | - | Atlético Madrid | 1:4 (1:2) | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: Atlético Madrid | ||||
| 1st(1st leg) | RC Lens | - | Vitesse | 4:1 (2:0) | ||
| 2nd (2nd leg) | Vitesse | - | RC Lens | 1:1 (0:0) | ||
| 1st(1st leg): 28/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: RC Lens | ||||
| 1st(1st leg) | Tottenham Hotspur | - | 1. FC Kaiserslautern | 1:0 (1:0) | ||
| 2nd (2nd leg) | 1. FC Kaiserslautern | - | Tottenham Hotspur | 2:0 (0:0) | ||
| 1st(1st leg): 28/10/1999 | 2nd (2nd leg): 04/11/1999 | Winner: 1. FC Kaiserslautern | ||||
