1. Round | 08/08/1999 | Fenerbahçe | - | Vanspor AS | 3:0 | ||||
2. Round | 15/08/1999 | Vanspor AS | - | Erzurumspor (1968-2015) | 0:2 | ||||
9. Round | 21/11/1999 | Vanspor AS | - | İstanbulspor AŞ | 1:1 | ||||
10. Round | 28/11/1999 | Gaziantepspor | - | Vanspor AS | 1:3 | ||||
11. Round | 05/12/1999 | Vanspor AS | - | Trabzonspor | 2:2 | ||||
12. Round | 12/12/1999 | MKE Ankaragücü | - | Vanspor AS | 1:0 | ||||
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 |