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| Qualifier | ||||||
|---|---|---|---|---|---|---|
| 09/05/2009 | 19:00 | KV Red Star Waasland | - | Lierse SK (old) | 1:1 | |
| 19:00 | RFC Tournai | - | Royal Antwerp FC | 0:0 | ||
| 16/05/2009 | 19:00 | Royal Antwerp FC | - | RFC Tournai | 2:0 | |
| 19:00 | Lierse SK (old) | - | KV Red Star Waasland | 3:2 | ||
| 1. Round | ||||||
| 24/05/2009 | 15:00 | Royal Antwerp FC | - | KSV Roeselare | 1:3 | |
| 15:00 | FCV Dender EH | - | Lierse SK (old) | 1:1 | ||
| 2. Round | ||||||
| 28/05/2009 | 19:30 | Lierse SK (old) | - | Royal Antwerp FC | 0:0 | |
| 19:30 | KSV Roeselare | - | FCV Dender EH | 0:0 | ||
| 3. Round | ||||||
| 31/05/2009 | 15:00 | KSV Roeselare | - | Lierse SK (old) | 1:0 | |
| 15:00 | Royal Antwerp FC | - | FCV Dender EH | 0:2 | ||
| 4. Round | ||||||
| 04/06/2009 | 19:30 | Lierse SK (old) | - | KSV Roeselare | 1:3 | |
| 19:30 | FCV Dender EH | - | Royal Antwerp FC | 1:2 | ||
| 5. Round | ||||||
| 07/06/2009 | 15:00 | KSV Roeselare | - | Royal Antwerp FC | 4:2 | |
| 15:00 | Lierse SK (old) | - | FCV Dender EH | 2:1 | ||
| 6. Round | ||||||
| 11/06/2009 | 19:30 | Royal Antwerp FC | - | Lierse SK (old) | 1:1 | |
| 19:30 | FCV Dender EH | - | KSV Roeselare | 3:2 | ||
