| 1. Round | 07/08/1999 | RSC Charleroi | - | KRC Harelbeke | 2:1 | ||||
| 2. Round | 14/08/1999 | KV Mechelen | - | RSC Charleroi | 2:1 | ||||
| 3. Round | 21/08/1999 | RSC Charleroi | - | KVC Westerlo | 1:2 | ||||
| 4. Round | 28/08/1999 | KAA Gent | - | RSC Charleroi | 3:2 | ||||
| 5. Round | 11/09/1999 | RSC Charleroi | - | KRC Genk | 2:1 | ||||
| 6. Round | 17/09/1999 | Standard Liège | - | RSC Charleroi | 1:3 |  |
|||
| 8. Round | 01/10/1999 | RSC Charleroi | - | Excelsior Mouscron | 2:1 | ||||
| 9. Round | 13/10/1999 | KSK Beveren | - | RSC Charleroi | 1:1 | ||||
| 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 | ||||
| 16. Round | 04/12/1999 | RSC Charleroi | - | K.S.C. Eendracht Aalst | 0:1 |
Belgium