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| 1st(1st leg) | KV Mechelen | - | KV Kortrijk | 1:0 | ||
| 2nd (2nd leg) | KV Kortrijk | - | KV Mechelen | 0:0 | ||
| 1st(1st leg): 27/01/2009 19:30 | 2nd (2nd leg): 17/02/2009 19:30 | Winner: KV Mechelen | ||||
| 1st(1st leg) | KRC Mechelen | - | Lierse SK | 1:0 | ||
| 2nd (2nd leg) | Lierse SK | - | KRC Mechelen | 3:0 | ||
| 1st(1st leg): 28/01/2009 19:30 | 2nd (2nd leg): 04/02/2009 19:30 | Winner: Lierse SK | ||||
| 1st(1st leg) | Cercle Brugge | - | KSV Roeselare | 1:0 | ||
| 2nd (2nd leg) | KSV Roeselare | - | Cercle Brugge | 2:1 | ||
| 1st(1st leg): 28/01/2009 19:30 | 2nd (2nd leg): 17/02/2009 19:30 | Winner: Cercle Brugge | ||||
| 1st(1st leg) | KAA Gent | - | KRC Genk | 1:0 | ||
| 2nd (2nd leg) | KRC Genk | - | KAA Gent | 2:0 aet | ||
| 1st(1st leg): 28/01/2009 19:45 | 2nd (2nd leg): 04/02/2009 19:45 | Winner: KRC Genk | ||||
