| 1. Round | 07/08/1999 | RSC Charleroi | - | KRC Harelbeke | 2:1 | ||||
| 3. Round | 21/08/1999 | RSC Charleroi | - | KVC Westerlo | 1:2 | ||||
| 10. Round | 23/10/1999 | RSC Charleroi | - | Lierse SK (old) | 1:1 | ||||
| 11. Round | 30/10/1999 | Lommelse SK | - | RSC Charleroi | 1:1 | ||||
| 12. Round | 05/11/1999 | RSC Charleroi | - | Club Brugge KV | 0:2 | ||||
| 13. Round | 10/11/1999 | Sint-Truidense VV | - | RSC Charleroi | 2:2 | ||||
| 14. Round | 20/11/1999 | RSC Charleroi | - | Sporting Lokeren | 2:4 |  |
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| 15. Round | 28/11/1999 | Germinal Beerschot | - | RSC Charleroi | 3:0 | ||||
| 16. Round | 04/12/1999 | RSC Charleroi | - | K.S.C. Eendracht Aalst | 0:1 | ||||
| 17. Round | 11/12/1999 | RSC Anderlecht | - | RSC Charleroi | 3:0 | ||||
| 18. Round | 12/01/2000 | KRC Harelbeke | - | RSC Charleroi | 4:1 | ||||
| 19. Round | 15/01/2000 | RSC Charleroi | - | KV Mechelen | 1:4 | ||||
| 20. Round | 23/01/2000 | KVC Westerlo | - | RSC Charleroi | 1:1 | ||||
| 21. Round | 29/01/2000 | RSC Charleroi | - | KAA Gent | 1:2 | ||||
| 22. Round | 05/02/2000 | KRC Genk | - | RSC Charleroi | 1:2 | ||||
| 23. Round | 13/02/2000 | RSC Charleroi | - | Standard Liège | 1:4 | ||||
| 24. Round | 19/02/2000 | RSC Charleroi | - | Verbroedering Geel | 1:3 |
Belgium