| 1. Round | 08/08/1999 | Fenerbahçe | - | Vanspor AS | 3:0 | ||||
| 2. Round | 15/08/1999 | Vanspor AS | - | Erzurumspor (1968-2015) | 0:2 | ||||
| 3. Round | 12/09/1999 | Gençlerbirliği | - | Vanspor AS | 1:1 | ||||
| 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 |  |
|||
| 18. Round | 28/01/2000 | Vanspor AS | - | Fenerbahçe | 1:2 |  |
Turkey