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 - Steaua Bucureşti 4:1 (2:0)
2nd (2nd leg) Steaua Bucureşti - 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 Piräus - Juventus 1:3 (1:1)
2nd (2nd leg) Juventus - Olympiakos Piräus 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) Celta Vigo - SL Benfica 7:0 (4:0)
2nd (2nd leg) SL Benfica - Celta Vigo 1:1 (0:1)
1st(1st leg): 25/11/1999 2nd (2nd leg): 09/12/1999 Winner: Celta Vigo
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