| 1. Round | 14/07/2019 | Krylia Sovetov [U20] | - | CSKA Moskva [U20] | 1:1 |  |
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| 2. Round | 20/07/2019 | Krylia Sovetov [U20] | - | Arsenal Tula [U20] | 5:1 | |
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| 3. Round | 26/07/2019 | FK Ufa [U20] | - | Krylia Sovetov [U20] | 1:6 | |
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| 4. Round | 02/08/2019 | Krylia Sovetov [U20] | - | Lokomotiv Moskva [U20] | 0:1 | ||||
| 5. Round | 12/08/2019 | FK Rostov [U20] | - | Krylia Sovetov [U20] | 1:3 | ||||
| 6. Round | 17/08/2019 | FK Ural [U20] | - | Krylia Sovetov [U20] | 2:2 | |
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| 7. Round | 24/08/2019 | Krylia Sovetov [U20] | - | Spartak Moskva [U20] | 4:1 | ||||
| 8. Round | 29/08/2019 | Krylia Sovetov [U20] | - | Dinamo Moskva [U20] | 0:3 | ||||
| 15. Round | 03/11/2019 | Krylia Sovetov [U20] | - | Rubin Kazan [U20] | 3:2 | |
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| 16. Round | 08/11/2019 | Spartak Moskva [U20] | - | Krylia Sovetov [U20] | 4:2 | |
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| 17. Round | 23/11/2019 | CSKA Moskva [U20] | - | Krylia Sovetov [U20] | 2:1 |  |
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| 20. Round | 29/02/2020 | Krylia Sovetov [U20] | - | FK Orenburg [U20] | 3:1 |
Russia