| 1. Round | 06/08/1999 | Galatasaray | - | Gaziantepspor | 1:2 | ||||
| 2. Round | 15/08/1999 | Trabzonspor | - | Galatasaray | 1:2 | ||||
| 3. Round | 11/09/1999 | Galatasaray | - | MKE Ankaragücü | 5:0 | ||||
| 4. Round | 17/09/1999 | Adanaspor | - | Galatasaray | 3:4 | ||||
| 6. Round | 15/10/1999 | Galatasaray | - | Antalyaspor | 2:0 | ||||
| 7. Round | 22/10/1999 | Bursaspor | - | Galatasaray | 0:0 | ||||
| 10. Round | 28/11/1999 | Galatasaray | - | Erzurumspor (1968-2015) | 4:1 | ||||
| 11. Round | 03/12/1999 | Gençlerbirliği | - | Galatasaray | 1:1 | ||||
| 13. Round | 18/12/1999 | Denizlispor | - | Galatasaray | 2:4 |
Turkey