| 1. Round | 07/08/1999 | Standard Liège | - | KV Mechelen | 2:1 | ||||
| 2. Round | 14/08/1999 | KV Mechelen | - | RSC Charleroi | 2:1 | ||||
| 3. Round | 21/08/1999 | Excelsior Mouscron | - | KV Mechelen | 2:0 | ||||
| 4. Round | 28/08/1999 | KV Mechelen | - | KSK Beveren | 3:1 | ||||
| 5. Round | 11/09/1999 | Lierse SK (old) | - | KV Mechelen | 5:1 |  |
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| 6. Round | 18/09/1999 | KV Mechelen | - | Lommelse SK | 1:0 | ||||
| 7. Round | 26/09/1999 | Club Brugge KV | - | KV Mechelen | 6:0 | ||||
| 9. Round | 13/10/1999 | Sporting Lokeren | - | KV Mechelen | 0:2 |
Belgium