All countries
| 1/16-finals | Parnu JK Vaprus | Keila JK | 9:0 (5:0, 4:0) | details | 19.08.2025 | |||
| 1/32-finals | Jarva-Jaani | Keila JK | 1:4 (0:1, 1:3) | details | 06.08.2025 | |||
| 1/64-finals | Keila JK | Kallaste United | 5:2 (1:0, 4:2) | details | 12.06.2025 | |||
| 1/32-finals | Flora U21 | Keila JK | 2:0 (1:0, 1:0) | details | 27.07.2023 | |||
| 1/64-finals | Keila JK | JK Jalgpallihaigla | 11:0 (6:0, 5:0) | details | 02.07.2023 | |||
| 30. Round | Keila JK | Nomme Kalju U21 | 3:3 | details | 21.11.2020 | |||
| 29. Round | Keila JK | JK Tarvas Rakvere | 0:1 | details | 09.11.2020 | |||
| 28. Round | Voru Helios | Keila JK | 2:2 | details | 31.10.2020 | |||
| 27. Round | Keila JK | Viimsi JK | 0:0 | details | 24.10.2020 | |||
| 26. Round | JK Tarvas Rakvere | Keila JK | 1:6 | details | 17.10.2020 | |||
| 25. Round | Keila JK | Paide Linnameeskond U21 | 3:6 | details | 03.10.2020 | |||
| 1/16-finals | Maardu | Keila JK | 5:3 (2:2, 3:1) | details | 29.09.2020 | |||
| 24. Round | Nomme Kalju U21 | Keila JK | 1:3 | details | 26.09.2020 | |||
| 23. Round | Tartu Welco | Keila JK | 6:1 | details | 20.09.2020 | |||
| 22. Round | Keila JK | Voru Helios | 1:3 | details | 17.09.2020 | |||
| 21. Round | Keila JK | Tabasalu | 0:1 | details | 13.09.2020 | |||
| 20. Round | Tallinna Kalev U21 | Keila JK | 3:1 | details | 06.09.2020 | |||
| 19. Round | Keila JK | Haapsalu | 3:4 | details | 23.08.2020 | |||
| 18. Round | Viimsi JK | Keila JK | 2:2 | details | 20.08.2020 | |||
| 17. Round | Keila JK | Tartu Welco | 1:3 | details | 16.08.2020 | |||
| 1/32-finals | Hiiumaa | Keila JK | 3:4 (1:3, 2:1) | details | 11.08.2020 | |||
| 16. Round | Haapsalu | Keila JK | 7:1 | details | 08.08.2020 | |||
| 15. Round | Keila JK | Voru Helios | 1:2 | details | 01.08.2020 | |||
| 14. Round | JK Tarvas Rakvere | Keila JK | 2:4 | details | 25.07.2020 | |||
| 13. Round | Keila JK | Paide Linnameeskond U21 | 4:4 | details | 19.07.2020 | |||
| 12. Round | Nomme Kalju U21 | Keila JK | 3:5 | details | 16.07.2020 | |||
| 11. Round | Tallinna Kalev U21 | Keila JK | 13:1 | details | 11.07.2020 | |||
| 10. Round | Keila JK | Tabasalu | 2:2 | details | 05.07.2020 | |||
| 9. Round | Paide Linnameeskond U21 | Keila JK | 5:3 | details | 02.07.2020 | |||
| 8. Round | Keila JK | JK Tarvas Rakvere | 4:1 | details | 28.06.2020 | |||
| 7. Round | Keila JK | Nomme Kalju U21 | 0:3 | details | 21.06.2020 | |||
| 6. Round | Tartu Welco | Keila JK | 6:1 | details | 18.06.2020 | |||
| 5. Round | Keila JK | Viimsi JK | 1:2 | details | 14.06.2020 | |||
| 4. Round | Voru Helios | Keila JK | 2:3 | details | 07.06.2020 | |||
| 3. Round | Tabasalu | Keila JK | 0:3 | details | 04.06.2020 | |||
| 2. Round | Keila JK | Tallinna Kalev U21 | 0:4 | details | 31.05.2020 | |||
| Keila JK | Parnu JK Vaprus | 3:3 (1:1, 2:2) | details | 23.05.2020 | ||||
| 1. Round | Keila JK | Haapsalu | 2:1 | details | 08.03.2020 | |||
| Keila JK | Haapsalu | 0:1 (0:1, 0:0) | details | 24.02.2020 | ||||
| Viimsi JK | Keila JK | 2:2 (1:0, 1:2) | details | 15.02.2020 | ||||
| Keila JK | Paide Linnameeskond U21 | 0:5 (0:4, 0:1) | details | 01.02.2020 | ||||
| Tabasalu | Keila JK | 5:2 (2:1, 3:1) | details | 26.01.2020 | ||||
| 36. Round | Paide Linnameeskond U21 | Keila JK | 2:4 | details | 10.11.2019 | |||
| 35. Round | Voru Helios | Keila JK | 0:3 | details | 02.11.2019 | |||
| 34. Round | Keila JK | Parnu | 1:0 | details | 27.10.2019 | |||
| 33. Round | Keila JK | Tabasalu | 1:1 | details | 20.10.2019 | |||
| 32. Round | Nomme Kalju U21 | Keila JK | 0:1 | details | 05.10.2019 | |||
| 31. Round | Nomme Utd | Keila JK | 6:1 | details | 28.09.2019 | |||
| 30. Round | Keila JK | Pohja-Tallinna JK Volta | 7:1 | details | 22.09.2019 | |||
| 29. Round | Keila JK | Vandra Vaprus | 1:4 | details | 19.09.2019 | |||