| 1. Round | 11/09/2020 | FK Chertanovo [U20] | - | Dinamo Moskva [U20] | 1:3 | ||||
| 2. Round | 16/09/2020 | FK Krasnodar [U20] | - | FK Chertanovo [U20] | 0:2 | ||||
| 3. Round | 22/09/2020 | Arsenal Tula [U20] | - | FK Chertanovo [U20] | 0:0 | ||||
| 5. Round | 03/10/2020 | FK Chertanovo [U20] | - | FK Tambov [U20] | 3:4 | ||||
| 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 | ||||
| 15. Round | 28/02/2021 | FK Chertanovo [U20] | - | Rotor Volgograd [U20] | 2:1 | ||||
| 16. Round | 03/03/2021 | FK Tambov [U20] | - | FK Chertanovo [U20] | 2:1 | ||||
| 18. Round | 17/03/2021 | FK Chertanovo [U20] | - | Arsenal Tula [U20] | 0:4 |
Russia