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| H | ÍBV Vestmannaeyjar | - | KF Tiranë | 1:0 (1:0) | ||
| R | KF Tiranë | - | ÍBV Vestmannaeyjar | 1:2 (0:2) | ||
| H: 13.07.1999 20:00 | R: 21.07.1999 17:30 | Sieger: ÍBV Vestmannaeyjar | ||||
| H | PFC Litex Lovech | - | Glentoran FC | 3:0 (2:0) | ||
| R | Glentoran FC | - | PFC Litex Lovech | 0:2 (0:0) | ||
| H: 14.07.1999 17:30 | R: 21.07.1999 20:30 | Sieger: PFC Litex Lovech | ||||
| H | FK Zalgiris | - | Tsement Ararat | 2:0 (1:0) | ||
| R | Tsement Ararat | - | FK Zalgiris | 0:3 (0:2) | ||
| H: 14.07.1999 17:30 | R: 21.07.1999 15:00 | Sieger: FK Zalgiris | ||||
| H | Partizan | - | FC Flora | 6:0 (3:0) | ||
| R | FC Flora | - | Partizan | 1:4 (0:2) | ||
| H: 14.07.1999 19:30 | R: 21.07.1999 18:00 | Sieger: Partizan | ||||
| H | Jeunesse Esch | - | Skonto FC | 0:2 (0:0) | ||
| R | Skonto FC | - | Jeunesse Esch | 8:0 (2:0) | ||
| H: 14.07.1999 19:30 | R: 21.07.1999 17:30 | Sieger: Skonto FC | ||||
| H | HB Tórshavn | - | Haka Valkeakoski | 1:1 (0:0) | ||
| R | Haka Valkeakoski | - | HB Tórshavn | 6:0 (2:0) | ||
| H: 14.07.1999 20:00 | R: 21.07.1999 18:00 | Sieger: Haka Valkeakoski | ||||
| H | FK Sloga Jugomagnat | - | FK Kapaz Gäncä | 1:0 (0:0) | ||
| R | FK Kapaz Gäncä | - | FK Sloga Jugomagnat | 2:1 (1:1) | ||
| H: 14.07.1999 20:00 | R: 21.07.1999 16:00 | Sieger: FK Sloga Jugomagnat | ||||
| H | Barry Town FC | - | Valletta FC | 0:0 (0:0) | ||
| R | Valletta FC | - | Barry Town FC | 3:2 (2:1) | ||
| H: 14.07.1999 20:30 | R: 21.07.1999 20:00 | Sieger: Valletta FC | ||||
| H | St Patrick's Athletic | - | FC Zimbru | 0:5 (0:3) | ||
| R | FC Zimbru | - | St Patrick's Athletic | 5:0 (3:0) | ||
| H: 14.07.1999 20:45 | R: 21.07.1999 17:00 | Sieger: FC Zimbru | ||||
