1st(1st leg) Aris Saloniki - Celta Vigo 2:2 (1:2)
2nd (2nd leg) Celta Vigo - Aris Saloniki 2:0 (0:0)
1st(1st leg): 19/10/1999 2nd (2nd leg): 04/11/1999 Winner: Celta Vigo
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) Inter Slovnaft Bratislava - FC Nantes 0:3 (0:2)
2nd (2nd leg) FC Nantes - 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) Steaua Bucureşti - West Ham United 2:0 (1:0)
2nd (2nd leg) West Ham United - Steaua Bucureşti 0:0 (0:0)
1st(1st leg): 21/10/1999 2nd (2nd leg): 04/11/1999 Winner: Steaua Bucureşti
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 Lyon - Celtic FC 1:0 (0:0)
2nd (2nd leg) Celtic FC - Olympique Lyon 0:1 (0:1)
1st(1st leg): 21/10/1999 2nd (2nd leg): 04/11/1999 Winner: Olympique Lyon
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