| 1. Round | 06/08/1999 | Verbroedering Geel | - | KAA Gent | 1:5 | ||||
| 2. Round | 14/08/1999 | Sint-Truidense VV | - | Verbroedering Geel | 1:1 |  |
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| 3. Round | 21/08/1999 | Verbroedering Geel | - | KRC Genk | 1:1 | ||||
| 4. Round | 28/08/1999 | Sporting Lokeren | - | Verbroedering Geel | 0:0 | |
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| 5. Round | 11/09/1999 | Verbroedering Geel | - | Standard Liège | 0:0 | ||||
| 6. Round | 18/09/1999 | Germinal Beerschot | - | Verbroedering Geel | 4:1 | |
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| 8. Round | 03/10/1999 | K.S.C. Eendracht Aalst | - | Verbroedering Geel | 1:0 | ||||
| 9. Round | 13/10/1999 | Verbroedering Geel | - | Excelsior Mouscron | 1:4 | ||||
| 10. Round | 24/10/1999 | RSC Anderlecht | - | Verbroedering Geel | 4:0 | ||||
| 11. Round | 30/10/1999 | Verbroedering Geel | - | KSK Beveren | 1:1 | ||||
| 12. Round | 07/11/1999 | KRC Harelbeke | - | Verbroedering Geel | 3:0 | ||||
| 13. Round | 10/11/1999 | Verbroedering Geel | - | Lierse SK (old) | 2:1 | ||||
| 14. Round | 20/11/1999 | KV Mechelen | - | Verbroedering Geel | 1:1 | ||||
| 16. Round | 04/12/1999 | Verbroedering Geel | - | KVC Westerlo | 2:3 | ||||
| 17. Round | 11/12/1999 | Club Brugge KV | - | Verbroedering Geel | 4:0 | ||||
| 20. Round | 22/01/2000 | KRC Genk | - | Verbroedering Geel | 1:0 |
Belgium