| 8. Round | 31/10/1999 | İstanbulspor AŞ | - | Denizlispor | 1:1 | ||||
| 9. Round | 21/11/1999 | Vanspor AS | - | İstanbulspor AŞ | 1:1 | ||||
| 10. Round | 28/11/1999 | İstanbulspor AŞ | - | Kocaelispor | 4:1 |  |
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| 11. Round | 05/12/1999 | Altay Izmir | - | İstanbulspor AŞ | 0:0 | ||||
| 12. Round | 11/12/1999 | İstanbulspor AŞ | - | Samsunspor | 0:1 | ||||
| 13. Round | 19/12/1999 | İstanbulspor AŞ | - | Gaziantepspor | 1:1 | ||||
| 14. Round | 26/12/1999 | Trabzonspor | - | İstanbulspor AŞ | 1:1 | ||||
| 15. Round | 09/01/2000 | İstanbulspor AŞ | - | MKE Ankaragücü | 2:6 | ||||
| 19. Round | 05/02/2000 | Bursaspor | - | İstanbulspor AŞ | 1:0 | ||||
| 20. Round | 13/02/2000 | İstanbulspor AŞ | - | Göztepe | 3:0 | |
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| 21. Round | 19/02/2000 | Fenerbahçe | - | İstanbulspor AŞ | 1:0 | ||||
| 22. Round | 27/02/2000 | İstanbulspor AŞ | - | Erzurumspor (1968-2015) | 1:1 | ||||
| 26. Round | 25/03/2000 | İstanbulspor AŞ | - | Vanspor AS | 0:0 | ||||
| 27. Round | 02/04/2000 | Kocaelispor | - | İstanbulspor AŞ | 2:1 |
Liberia