1. Round | 18/08/2019 | BB Erzurumspor | - | İstanbulspor AŞ | 2:2 | ||||
2. Round | 26/08/2019 | İstanbulspor AŞ | - | Altay Izmir | 2:2 | ||||
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 | ||||
7. Round | 05/10/2019 | İstanbulspor AŞ | - | Keçiörengücü | 1:1 | ||||
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 | ||||
12. Round | 24/11/2019 | Hatayspor | - | İstanbulspor AŞ | 1:0 | ||||
13. Round | 29/11/2019 | İstanbulspor AŞ | - | Fatih Karagümrük | 4:0 | ||||
14. Round | 07/12/2019 | Akhisar Belediyespor | - | İstanbulspor AŞ | 4:3 |