| 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 | ||||
| 10. Round | 28/11/1999 | Gaziantepspor | - | Vanspor AS | 1:3 | ||||
| 14. Round | 26/12/1999 | Galatasaray | - | Vanspor AS | 2:1 | |
|||
| 15. Round | 09/01/2000 | Vanspor AS | - | Antalyaspor | 2:4 | ||||
| 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 |
Turkey