| 3. Round | 21/08/1999 | Standard Liège | - | KAA Gent | 0:2 | ||||
| 6. Round | 18/09/1999 | KAA Gent | - | KSK Beveren | 4:1 | ||||
| 7. Round | 25/09/1999 | Lierse SK (old) | - | KAA Gent | 2:1 | ||||
| 8. Round | 02/10/1999 | KAA Gent | - | Lommelse SK | 6:2 | ||||
| 9. Round | 13/10/1999 | Club Brugge KV | - | KAA Gent | 1:3 | ||||
| 10. Round | 23/10/1999 | KAA Gent | - | Sint-Truidense VV | 4:2 | ||||
| 11. Round | 30/10/1999 | Sporting Lokeren | - | KAA Gent | 0:4 | ||||
| 13. Round | 10/11/1999 | K.S.C. Eendracht Aalst | - | KAA Gent | 4:2 | ||||
| 14. Round | 19/11/1999 | KAA Gent | - | RSC Anderlecht | 0:3 | ||||
| 15. Round | 28/11/1999 | KRC Harelbeke | - | KAA Gent | 1:2 | ||||
| 16. Round | 05/12/1999 | KAA Gent | - | KV Mechelen | 6:1 | ||||
| 17. Round | 11/12/1999 | KVC Westerlo | - | KAA Gent | 4:2 |
Belgium