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 | ||||
7. Round | 24/10/1999 | Vanspor AS | - | Kocaelispor | 5:0 | ||||
8. Round | 31/10/1999 | Altay Izmir | - | Vanspor AS | 2:0 | ||||
10. Round | 28/11/1999 | Gaziantepspor | - | Vanspor AS | 1:3 | ||||
11. Round | 05/12/1999 | Vanspor AS | - | Trabzonspor | 2:2 | ||||
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 | ||||
16. Round | 15/01/2000 | Bursaspor | - | Vanspor AS | 3:2 |