| 1. Round | 08/08/1999 | Fenerbahçe | - | Vanspor AS | 3:0 | ||||
| 4. Round | 19/09/1999 | İstanbulspor AŞ | - | Fenerbahçe | 1:4 | ||||
| 5. Round | 26/09/1999 | Fenerbahçe | - | Gaziantepspor | 0:0 | ||||
| 6. Round | 16/10/1999 | Trabzonspor | - | Fenerbahçe | 2:0 | ||||
| 7. Round | 24/10/1999 | Fenerbahçe | - | MKE Ankaragücü | 1:1 | ||||
| 8. Round | 30/10/1999 | Adanaspor | - | Fenerbahçe | 1:3 | ||||
| 11. Round | 05/12/1999 | Fenerbahçe | - | Bursaspor | 2:2 | ||||
| 12. Round | 11/12/1999 | Göztepe | - | Fenerbahçe | 0:0 | ||||
| 13. Round | 17/12/1999 | Samsunspor | - | Fenerbahçe | 1:1 | ||||
| 9. Round | 22/12/1999 | Fenerbahçe | - | Galatasaray | 1:2 |
Turkey