| 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 | ||||
| 4. Round | 19/09/1999 | Vanspor AS | - | Beşiktaş | 0:6 | ||||
| 5. Round | 26/09/1999 | Denizlispor | - | Vanspor AS | 1:0 | ||||
| 7. Round | 24/10/1999 | Vanspor AS | - | Kocaelispor | 5:0 | ||||
| 8. Round | 31/10/1999 | Altay Izmir | - | Vanspor AS | 2:0 | ||||
| 16. Round | 15/01/2000 | Bursaspor | - | Vanspor AS | 3:2 | ||||
| 18. Round | 28/01/2000 | Vanspor AS | - | Fenerbahçe | 1:2 | ||||
| 17. Round | 02/02/2000 | Vanspor AS | - | Göztepe | 1:0 | ||||
| 19. Round | 06/02/2000 | Erzurumspor (1968-2015) | - | Vanspor AS | 2:0 | ||||
| 20. Round | 12/02/2000 | Vanspor AS | - | Gençlerbirliği | 2:5 |  |
|||
| 21. Round | 18/02/2000 | Beşiktaş | - | Vanspor AS | 2:1 |  |
|||
| 22. Round | 27/02/2000 | Vanspor AS | - | Denizlispor | 2:3 | ||||
| 23. Round | 05/03/2000 | Samsunspor | - | Vanspor AS | 5:1 | ||||
| 25. Round | 19/03/2000 | Vanspor AS | - | Altay Izmir | 1:1 | ||||
| 26. Round | 25/03/2000 | İstanbulspor AŞ | - | Vanspor AS | 0:0 | ||||
| 27. Round | 01/04/2000 | Vanspor AS | - | Gaziantepspor | 1:2 | ||||
| 28. Round | 09/04/2000 | Trabzonspor | - | Vanspor AS | 4:2 |
Turkey