| 1. Round | 08/08/1999 | Adanaspor | - | Trabzonspor | 1:2 | ||||
| 2. Round | 15/08/1999 | MKE Ankaragücü | - | Adanaspor | 0:0 | ||||
| 5. Round | 26/09/1999 | Antalyaspor | - | Adanaspor | 2:2 | ||||
| 8. Round | 30/10/1999 | Adanaspor | - | Fenerbahçe | 1:3 | ||||
| 12. Round | 10/12/1999 | Adanaspor | - | Denizlispor | 3:2 |  |
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| 13. Round | 19/12/1999 | Vanspor AS | - | Adanaspor | 0:2 | ||||
| 14. Round | 25/12/1999 | Adanaspor | - | Kocaelispor | 3:0 | ||||
| 15. Round | 08/01/2000 | Altay Izmir | - | Adanaspor | 2:1 | ||||
| 17. Round | 22/01/2000 | Gaziantepspor | - | Adanaspor | 1:1 | ||||
| 21. Round | 20/02/2000 | Galatasaray | - | Adanaspor | 4:0 | ||||
| 24. Round | 12/03/2000 | Adanaspor | - | Göztepe | 2:0 | |
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| 25. Round | 17/03/2000 | Fenerbahçe | - | Adanaspor | 2:4 | ||||
| 26. Round | 25/03/2000 | Adanaspor | - | Erzurumspor (1968-2015) | 2:0 | ||||
| 27. Round | 01/04/2000 | Gençlerbirliği | - | Adanaspor | 5:2 | ||||
| 28. Round | 08/04/2000 | Adanaspor | - | Beşiktaş | 1:3 | |
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| 29. Round | 15/04/2000 | Denizlispor | - | Adanaspor | 4:2 | ||||
| 30. Round | 22/04/2000 | Adanaspor | - | Vanspor AS | 2:0 | |
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| 32. Round | 07/05/2000 | Adanaspor | - | Altay Izmir | 1:0 | ||||
| 33. Round | 12/05/2000 | İstanbulspor AŞ | - | Adanaspor | 3:2 |
Bulgaria