| 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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| 6. Round | 18/09/1999 | Germinal Beerschot | - | Verbroedering Geel | 4:1 | ||||
| 7. Round | 26/09/1999 | Verbroedering Geel | - | RSC Charleroi | 0:0 |  |
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| 8. Round | 03/10/1999 | K.S.C. Eendracht Aalst | - | Verbroedering Geel | 1:0 | |
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| 13. Round | 10/11/1999 | Verbroedering Geel | - | Lierse SK (old) | 2:1 | |
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| 15. Round | 27/11/1999 | Verbroedering Geel | - | Lommelse SK | 0:0 | ||||
| 16. Round | 04/12/1999 | Verbroedering Geel | - | KVC Westerlo | 2:3 | ||||
| 17. Round | 11/12/1999 | Club Brugge KV | - | Verbroedering Geel | 4:0 | |
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| 18. Round | 12/01/2000 | KAA Gent | - | Verbroedering Geel | 1:1 | |
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| 19. Round | 15/01/2000 | Verbroedering Geel | - | Sint-Truidense VV | 1:2 |
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