| 1. Round | 31/07/2019 | SK Dnipro-1 | - | Olimpik Donetsk | 2:0 | ||||
| 2. Round | 04/08/2019 | Olimpik Donetsk | - | Kolos Kovalivka | 0:1 | ||||
| 3. Round | 10/08/2019 | FK Oleksandriya | - | Olimpik Donetsk | 2:1 |  |
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| 4. Round | 18/08/2019 | Olimpik Donetsk | - | Karpaty Lviv | 1:3 | |
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| 6. Round | 01/09/2019 | Olimpik Donetsk | - | Shakhtar Donetsk | 0:4 | ||||
| 7. Round | 15/09/2019 | FK Mariupol | - | Olimpik Donetsk | 1:1 | ||||
| 8. Round | 21/09/2019 | FK Lviv | - | Olimpik Donetsk | 0:1 | ||||
| 10. Round | 05/10/2019 | Desna Chernigov | - | Olimpik Donetsk | 1:0 | |
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| 17. Round | 06/12/2019 | Shakhtar Donetsk | - | Olimpik Donetsk | 3:0 |
Ukraine