1st(1st leg) Olympique Lyonnais - Maribor Teatanic 0:1 (0:0)
2nd (2nd leg) Maribor Teatanic - Olympique Lyonnais 2:0 (2:0)
1st(1st leg): 10/08/1999 19:30 2nd (2nd leg): 25/08/1999 19:30 Winner: Maribor Teatanic
1st(1st leg) Spartak Moskva - Partizan 2:0 (1:0)
2nd (2nd leg) Partizan - Spartak Moskva 1:3 (0:1)
1st(1st leg): 11/08/1999 17:00 2nd (2nd leg): 25/08/1999 19:15 Winner: Spartak Moskva
1st(1st leg) FK Teplice - Borussia Dortmund 0:1 (0:0)
2nd (2nd leg) Borussia Dortmund - FK Teplice 1:0 (0:0)
1st(1st leg): 11/08/1999 17:00 2nd (2nd leg): 25/08/1999 19:30 Winner: Borussia Dortmund
1st(1st leg) Aalborg BK - Dinamo Kiev 1:2 (0:2)
2nd (2nd leg) Dinamo Kiev - Aalborg BK 2:2 (0:1)
1st(1st leg): 11/08/1999 17:30 2nd (2nd leg): 25/08/1999 17:00 Winner: Dinamo Kiev
1st(1st leg) FC Zimbru - PSV Eindhoven 0:0 (0:0)
2nd (2nd leg) PSV Eindhoven - FC Zimbru 2:0 (2:0)
1st(1st leg): 11/08/1999 18:30 2nd (2nd leg): 25/08/1999 19:00 Winner: PSV Eindhoven
1st(1st leg) Rapid Wien - Galatasaray 0:3 (0:2)
2nd (2nd leg) Galatasaray - Rapid Wien 1:0 (0:0)
1st(1st leg): 11/08/1999 18:30 2nd (2nd leg): 25/08/1999 19:30 Winner: Galatasaray
1st(1st leg) Hapoel Haifa - Valencia CF 0:2 (0:0)
2nd (2nd leg) Valencia CF - Hapoel Haifa 2:0 (0:0)
1st(1st leg): 11/08/1999 18:30 2nd (2nd leg): 25/08/1999 21:00 Winner: Valencia CF
1st(1st leg) Molde FK - RCD Mallorca 0:0 (0:0)
2nd (2nd leg) RCD Mallorca - Molde FK 1:1 (1:0)
1st(1st leg): 11/08/1999 19:00 2nd (2nd leg): 25/08/1999 20:30 Winner: Molde FK
1st(1st leg) AEK Athen - AIK Solna 0:0 (0:0)
2nd (2nd leg) AIK Solna - AEK Athen 1:0 (0:0)
1st(1st leg): 11/08/1999 19:15 2nd (2nd leg): 25/08/1999 18:00 Winner: AIK Solna
1st(1st leg) Croatia Zagreb - MTK Hungaria 0:0 (0:0)
2nd (2nd leg) MTK Hungaria - Croatia Zagreb 0:2 (0:0)
1st(1st leg): 11/08/1999 19:15 2nd (2nd leg): 25/08/1999 19:15 Winner: Croatia Zagreb
1st(1st leg) ACF Fiorentina - Widzew Łódź 3:1 (1:0)
2nd (2nd leg) Widzew Łódź - ACF Fiorentina 0:2 (0:1)
1st(1st leg): 11/08/1999 19:45 2nd (2nd leg): 25/08/1999 17:00 Winner: ACF Fiorentina
1st(1st leg) Brøndby IF - Boavista 1:2 (0:1)
2nd (2nd leg) Boavista - Brøndby IF 4:2 (1:0, 1:2, 4:2) aet
1st(1st leg): 11/08/1999 19:45 2nd (2nd leg): 25/08/1999 21:00 Winner: Boavista
1st(1st leg) Hertha BSC - Anorthosis Famagusta 2:0 (1:0)
2nd (2nd leg) Anorthosis Famagusta - Hertha BSC 0:0 (0:0)
1st(1st leg): 11/08/1999 19:45 2nd (2nd leg): 25/08/1999 17:00 Winner: Hertha BSC
1st(1st leg) Chelsea FC - Skonto FC 3:0 (0:0)
2nd (2nd leg) Skonto FC - Chelsea FC 0:0 (0:0)
1st(1st leg): 11/08/1999 20:05 2nd (2nd leg): 25/08/1999 17:30 Winner: Chelsea FC
1st(1st leg) Rangers FC - Parma AC 2:0 (1:0)
2nd (2nd leg) Parma AC - Rangers FC 1:0 (0:0)
1st(1st leg): 11/08/1999 20:05 2nd (2nd leg): 25/08/1999 20:00 Winner: Rangers FC
1st(1st leg) Sturm Graz - Servette FC 2:1 (2:1)
2nd (2nd leg) Servette FC - Sturm Graz 2:2 (0:0)
1st(1st leg): 11/08/1999 20:15 2nd (2nd leg): 25/08/1999 19:45 Winner: Sturm Graz