| 1. Round | 18/08/2019 | BB Erzurumspor | - | İstanbulspor AŞ | 2:2 |  |
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| 2. Round | 26/08/2019 | İstanbulspor AŞ | - | Altay Izmir | 2:2 | |
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| 3. Round | 31/08/2019 | Ümraniyespor | - | İstanbulspor AŞ | 2:1 | ||||
| 4. Round | 15/09/2019 | İstanbulspor AŞ | - | Giresunspor | 2:1 | ||||
| 5. Round | 20/09/2019 | İstanbulspor AŞ | - | Balıkesirspor | 2:2 | ||||
| 6. Round | 28/09/2019 | Boluspor | - | İstanbulspor AŞ | 1:2 | |
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| 7. Round | 05/10/2019 | İstanbulspor AŞ | - | Keçiörengücü | 1:1 | |
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| 9. Round | 26/10/2019 | İstanbulspor AŞ | - | Bursaspor | 1:2 | ||||
| 10. Round | 03/11/2019 | Altınordu FK | - | İstanbulspor AŞ | 1:1 | ||||
| 11. Round | 09/11/2019 | İstanbulspor AŞ | - | Menemen Belediyespor | 1:2 | |
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| 12. Round | 24/11/2019 | Hatayspor | - | İstanbulspor AŞ | 1:0 | |
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| 13. Round | 29/11/2019 | İstanbulspor AŞ | - | Fatih Karagümrük | 4:0 | ||||
| 14. Round | 07/12/2019 | Akhisar Belediyespor | - | İstanbulspor AŞ | 4:3 |
Turkey