| 1. Round | 28/07/2023 | FK Obolon | - | Kolos Kovalivka | 0:0 | ||||
| 2. Round | 04/08/2023 | FK Obolon | - | Dinamo Kiev | 2:4 | ||||
| 3. Round | 12/08/2023 | Chernomorets Odessa | - | FK Obolon | 2:0 | ||||
| 4. Round | 20/08/2023 | SK Dnipro-1 | - | FK Obolon | 1:2 | ||||
| 5. Round | 28/08/2023 | FK Obolon | - | Kryvbas Kryvyi Rih | 0:0 | ||||
| 6. Round | 02/09/2023 | Polissya Zhytomyr | - | FK Obolon | 2:0 | ||||
| 18. Round | 26/02/2024 | FK Obolon | - | Chernomorets Odessa | 1:1 | ||||
| 19. Round | 03/03/2024 | FK Obolon | - | SK Dnipro-1 | 0:1 | ||||
| 20. Round | 09/03/2024 | Kryvbas Kryvyi Rih | - | FK Obolon | 1:0 | ||||
| 24. Round | 13/04/2024 | FK Obolon | - | FC Mynai | 1:1 | ||||
| 15. Round | 17/04/2024 | FK Oleksandriya | - | FK Obolon | 2:2 | ||||
| 25. Round | 22/04/2024 | Metalist 1925 Kharkiv | - | FK Obolon | 1:1 | ||||
| 26. Round | 28/04/2024 | Zorya Lugansk | - | FK Obolon | 0:0 |
Ukraine