Russian Cup 2024/25, 1/128 finals |
| 21.08.2024 | | Luki-Energiya (Velikiye Luki) | | FK Kaluga (Kaluga) | | 2:1 (0:1) |
| Velikiye Luki |
Russian Cup 2023/24, 1/64 finals |
| 13.09.2023 | | Dynamo (Bryansk) | | FK Kaluga (Kaluga) | | 0:0, pen. 5:4 |
| Bryansk |
Russian Cup 2023/24, 1/128 finals |
| 23.08.2023 | | Kvant (Obninsk) | | FK Kaluga (Kaluga) | | 0:2 (0:1) |
| Obninsk |
Russian Cup 2022/23, 1/128 finals |
| 31.08.2022 | | FK Strogino (Moscow) | | FK Kaluga (Kaluga) | | 3:2 (0:1) |
| Moscow |
Russian Cup 2021/22, 1/128 finals |
| 28.07.2021 | | Kairat (Moscow) | | FK Kaluga (Kaluga) | | 1:0 (1:0) * |
| Moscow |
Russian Cup 2020/21, 1/64 finals |
| 02.09.2020 | | FK Kaluga (Kaluga) | | Salyut (Belgorod) | | 0:0, pen. 6:7 |
| Kaluga |
Russian Cup 2020/21, 1/128 finals |
| 19.08.2020 | | Avangard (Kursk) | | FK Kaluga (Kaluga) | | 1:2 (1:1) |
| Kursk |
Russian Cup 2020/21, 1/256 finals |
| 05.08.2020 | | FK Kaluga (Kaluga) | | FK Smolensk (Smolensk) | | 3:2 (2:1) |
| Kaluga |
Russian Cup 2019/20, 1/64 finals |
| 05.08.2019 | | FK Kaluga (Kaluga) | | Salyut-Belgorod (Belgorod) | | 3:3 aet (2:1, 3:3), pen. 4:5 |
| Kaluga |
Russian Cup 2019/20, 1/128 finals |
| 28.07.2019 | | Dynamo (Bryansk) | | FK Kaluga (Kaluga) | | 0:1 (0:0) |
| Bryansk |
Russian Cup 2018/19, 1/32 finals |
| 22.08.2018 | | FK Kaluga (Kaluga) | | FK Tambov (Tambov) | | 4:4 aet (1:2, 3:3), pen. 2:4 |
| Kaluga |
Russian Cup 2018/19, 1/64 finals |
| 07.08.2018 | | Dnepr (Smolensk) | | FK Kaluga (Kaluga) | | 1:2 (0:1) |
| Smolensk |
Russian Cup 2018/19, 1/128 finals |
| 30.07.2018 | | FK Kaluga (Kaluga) | | Veles (Moscow) | | 2:1 (0:0) |
| Kaluga Vilsy Stadium |
Russian Cup 2017/18, 1/64 finals |
| 07.08.2017 | | FK Kaluga (Kaluga) | | Energomash (Belgorod) | | 1:2 (0:1) |
| Kaluga |
Russian Cup 2017/18, 1/128 finals |
| 23.07.2017 | | Khimik (Novomoskovsk) | | FK Kaluga (Kaluga) | | 0:3 (0:3) |
| Novomoskovsk |
Russian Cup 2016/17, 1/32 finals |
| 24.08.2016 | | FK Kaluga (Kaluga) | | FK Tambov (Tambov) | | 1:3 (1:0) |
| Kaluga |
Russian Cup 2016/17, 1/64 finals |
| 07.08.2016 | | Vityaz (Podolsk) | | FK Kaluga (Kaluga) | | 3:5 (0:4) |
| Podolsk |
Russian Cup 2016/17, 1/128 finals |
| 24.07.2016 | | FK Kaluga (Kaluga) | | FK Strogino (Moscow) | | 5:1 (3:0) |
| Kaluga |
Russian Cup 2015/16, 1/256 finals |
| 15.07.2015 | | FK Chertanovo (Moscow) | | FK Kaluga (Kaluga) | | 4:0 (1:0) |
| Moscow |
Russian Cup 2014/15, 1/64 finals |
| 12.08.2014 | | Tekstilshchik (Ivanovo) | | FK Kaluga (Kaluga) | | 3:0 (3:0) |
| Ivanovo |
Russian Cup 2014/15, 1/128 finals |
| 29.07.2014 | | FK Kaluga (Kaluga) | | FK Dolgoprudny (Dolgoprudny) | | 2:1 (1:1) |
| Kaluga |
Russian Cup 2013/14, 1/128 finals |
| 26.07.2013 | | FK Kaluga (Kaluga) | | Zvezda (Ryazan) | | 1:2 (1:1) |
| Kaluga |
Russian Cup 2012/13, 1/32 finals |
| 01.09.2012 | | FK Kaluga (Kaluga) | | Torpedo (Moscow) | | 0:1 (0:1) |
| Kaluga |
Russian Cup 2012/13, 1/64 finals |
| 18.08.2012 | | FK Kaluga (Kaluga) | | Vityaz (Podolsk) | | 5:1 (2:1) |
| Kaluga |
Russian Cup 2012/13, 1/128 finals |
| 05.08.2012 | | FK Oryol (Oryol) | | FK Kaluga (Kaluga) | | 0:1 aet (0:0, 0:0) |
| Orel |
Russian Cup 2012/13, 1/256 finals |
| 11.07.2012 | | FK Kaluga (Kaluga) | | Podolye (Podolsk Region) | | 4:1 (3:0) |
| Kaluga |
Russian Cup 2011/12, 1/128 finals |
| 12.05.2011 | | FK Kaluga (Kaluga) | | Vityaz (Podolsk) | | 1:1 aet (1:1, 1:1), pen. 4:5 |
| Kaluga |
Russian Cup 2011/12, 1/256 finals |
| 22.04.2011 | | Podolye (Podolsk Region) | | FK Kaluga (Kaluga) | | 0:0 aet, pen. 3:5 |
| Podolsk |
Russian Cup 2010/11, 1/256 finals |
| 29.04.2010 | | Zvezda (Ryazan) | | FK Kaluga (Kaluga) | | 2:1 (0:1) |
| Ryazan |