| 1. Round | 22/07/2023 | FK Kaluga | - | SKA-Khabarovsk 2 | 1:0 | ||||
| 2. Round | 29/07/2023 | FK Khimki 2 | - | FK Kaluga | 1:3 | ||||
| 4. Round | 13/08/2023 | FK Kaluga | - | Kosmos Dolgoprudny | 2:0 | ||||
| 6. Round | 27/08/2023 | FK Kaluga | - | FK Znamya Noginsk | 7:1 | ||||
| 10. Round | 25/09/2023 | FK Kaluga | - | FK Sakhalinets | 1:1 | ||||
| 12. Round | 07/10/2023 | FK Kaluga | - | Spartak Tambov | 5:0 |
Russia