| 4. Round | 29/09/2020 | FK Chertanovo [U20] | - | FK Rostov [U20] | 1:1 | ||||
| 8. Round | 28/10/2020 | Rotor Volgograd [U20] | - | FK Chertanovo [U20] | 1:1 | ||||
| 9. Round | 05/11/2020 | FK Chertanovo [U20] | - | Akhmat Grozny [U20] | 1:3 |  |
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| 10. Round | 19/11/2020 | FK Rostov [U20] | - | FK Chertanovo [U20] | 2:1 | |
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| 11. Round | 25/11/2020 | Dinamo Moskva [U20] | - | FK Chertanovo [U20] | 11:3 | ||||
| 12. Round | 01/12/2020 | FK Chertanovo [U20] | - | Spartak Moskva [U20] | 1:4 | ||||
| 13. Round | 09/12/2020 | FK Sochi [U20] | - | FK Chertanovo [U20] | 4:1 | ||||
| 16. Round | 03/03/2021 | FK Tambov [U20] | - | FK Chertanovo [U20] | 2:1 | |
 |
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| 17. Round | 10/03/2021 | FK Chertanovo [U20] | - | FK Krasnodar [U20] | 1:3 | ||||
| 18. Round | 17/03/2021 | FK Chertanovo [U20] | - | Arsenal Tula [U20] | 0:4 |
Russia