| 1. Round | 08/08/1999 | Erzurumspor (1968-2015) | - | Denizlispor | 0:1 | ||||
| 2. Round | 15/08/1999 | Vanspor AS | - | Erzurumspor (1968-2015) | 0:2 |  |
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| 3. Round | 12/09/1999 | Erzurumspor (1968-2015) | - | Kocaelispor | 3:3 | ||||
| 4. Round | 19/09/1999 | Altay Izmir | - | Erzurumspor (1968-2015) | 3:0 | ||||
| 5. Round | 26/09/1999 | Erzurumspor (1968-2015) | - | İstanbulspor AŞ | 0:0 | ||||
| 6. Round | 17/10/1999 | Gaziantepspor | - | Erzurumspor (1968-2015) | 6:0 | ||||
| 7. Round | 24/10/1999 | Erzurumspor (1968-2015) | - | Trabzonspor | 2:1 | ||||
| 8. Round | 30/10/1999 | MKE Ankaragücü | - | Erzurumspor (1968-2015) | 1:0 | ||||
| 9. Round | 21/11/1999 | Erzurumspor (1968-2015) | - | Adanaspor | 4:1 |  |
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| 10. Round | 28/11/1999 | Galatasaray | - | Erzurumspor (1968-2015) | 4:1 | |
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| 12. Round | 12/12/1999 | Bursaspor | - | Erzurumspor (1968-2015) | 4:2 | ||||
| 15. Round | 08/01/2000 | Erzurumspor (1968-2015) | - | Samsunspor | 1:0 | ||||
| 16. Round | 16/01/2000 | Erzurumspor (1968-2015) | - | Gençlerbirliği | 1:1 | ||||
| 17. Round | 23/01/2000 | Beşiktaş | - | Erzurumspor (1968-2015) | 2:0 |
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