| 1. Round | 08/08/1999 | Fenerbahçe | - | Vanspor AS | 3:0 |  |
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| 2. Round | 15/08/1999 | Vanspor AS | - | Erzurumspor (1968-2015) | 0:2 | ||||
| 3. Round | 12/09/1999 | Gençlerbirliği | - | Vanspor AS | 1:1 | |
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| 4. Round | 19/09/1999 | Vanspor AS | - | Beşiktaş | 0:6 | ||||
| 5. Round | 26/09/1999 | Denizlispor | - | Vanspor AS | 1:0 | ||||
| 6. Round | 17/10/1999 | Vanspor AS | - | Samsunspor | 0:0 | ||||
| 7. Round | 24/10/1999 | Vanspor AS | - | Kocaelispor | 5:0 | ||||
| 8. Round | 31/10/1999 | Altay Izmir | - | Vanspor AS | 2:0 | ||||
| 13. Round | 19/12/1999 | Vanspor AS | - | Adanaspor | 0:2 | ||||
| 14. Round | 26/12/1999 | Galatasaray | - | Vanspor AS | 2:1 | ||||
| 15. Round | 09/01/2000 | Vanspor AS | - | Antalyaspor | 2:4 |
Turkey