World: Club Friendly - Main |
| | Bashkimi | Milano Kumanovo | CAN. | details | 13.04.2021 |
North Macedonia: Macedonian Cup - Main |
| 1/16-finals - 1. Round | KF Gostivar | Milano Kumanovo | 3:0 AWA. | details | 18.08.2010 |
North Macedonia: First League - Relegation |
| Final | Bregalnica Stip | Milano Kumanovo | 2:1 ET | details | 30.05.2010 |
North Macedonia: First League - Main |
| 31. Round | Pobeda | Milano Kumanovo | CAN. | details | 15.05.2010 |
| 30. Round | Milano Kumanovo | Vardar | 0:5 | details | 12.05.2010 |
| 29. Round | Turnovo | Milano Kumanovo | 2:1 | details | 09.05.2010 |
| 28. Round | Milano Kumanovo | Teteks | 2:4 | details | 30.04.2010 |
| 27. Round | Renova | Milano Kumanovo | 1:0 | details | 23.04.2010 |
| 26. Round | Milano Kumanovo | Rabotnicki | 0:2 | details | 18.04.2010 |
| 25. Round | Met. Skopje | Milano Kumanovo | 3:0 | details | 11.04.2010 |
| 24. Round | Milano Kumanovo | Pelister | 2:2 | details | 03.04.2010 |
| 23. Round | Sileks | Milano Kumanovo | 1:1 | details | 28.03.2010 |
| 22. Round | Milano Kumanovo | Met. Skopje | 0:0 | details | 24.03.2010 |
| 21. Round | Shkupi | Milano Kumanovo | CAN. | details | 21.03.2010 |
| 20. Round | Milano Kumanovo | Pobeda | 3:2 CAN. | details | 07.03.2010 |
| 19. Round | Vardar | Milano Kumanovo | 2:0 | details | 27.02.2010 |
| 18. Round | Milano Kumanovo | Makedonija GP | CAN. | details | 13.12.2009 |
| 17. Round | Teteks | Milano Kumanovo | 6:0 | details | 09.12.2009 |
| 16. Round | Milano Kumanovo | Sileks | 1:3 | details | 06.12.2009 |
| 15. Round | Turnovo | Milano Kumanovo | 3:1 | details | 29.11.2009 |
| 14. Round | Milano Kumanovo | Pelister | 3:0 | details | 22.11.2009 |
| 13. Round | Rabotnicki | Milano Kumanovo | 5:1 | details | 07.11.2009 |
| 12. Round | Renova | Milano Kumanovo | 4:0 | details | 04.11.2009 |
| 11. Round | Met. Skopje | Milano Kumanovo | 4:0 | details | 01.11.2009 |
| 10. Round | Milano Kumanovo | Shkupi | 0:3 | details | 26.10.2009 |
| 9. Round | Pobeda | Milano Kumanovo | 4:1 CAN. | details | 18.10.2009 |
| 8. Round | Milano Kumanovo | Vardar | 0:4 | details | 04.10.2009 |
| 7. Round | Makedonija GP | Milano Kumanovo | 8:0 | details | 26.09.2009 |
| 6. Round | Milano Kumanovo | Teteks | 1:5 | details | 19.09.2009 |
| 5. Round | Sileks | Milano Kumanovo | 4:0 | details | 13.09.2009 |
North Macedonia: Macedonian Cup - Main |
| 1/16-finals - 1. Round | Belasica | Milano Kumanovo | 3:1 | details | 26.08.2009 |
North Macedonia: First League - Main |
| 4. Round | Milano Kumanovo | Turnovo | 0:2 | details | 23.08.2009 |
| 3. Round | Pelister | Milano Kumanovo | 3:1 | details | 16.08.2009 |
| 2. Round | Milano Kumanovo | Rabotnicki | 0:2 | details | 12.08.2009 |
| 1. Round | Milano Kumanovo | Renova | 0:2 | details | 01.08.2009 |
Europe: Europa League - Qualification |
| Quarter-finals - 2nd leg - 2. Round | Slaven Belupo | Milano Kumanovo | 8:2 (2:0, 6:2) | details | 23.07.2009 |
| Quarter-finals - 1st leg - 2. Round | Milano Kumanovo | Slaven Belupo | 0:4 (0:4, 0:0) | details | 16.07.2009 |
North Macedonia: First League - Main |
| 33. Round | Met. Skopje | Milano Kumanovo | 0:1 | details | 31.05.2009 |
| 32. Round | Milano Kumanovo | Makedonija GP | 2:0 | details | 27.05.2009 |
| 31. Round | Renova | Milano Kumanovo | 4:1 | details | 17.05.2009 |
| 30. Round | Milano Kumanovo | Sileks | 3:2 | details | 10.05.2009 |
North Macedonia: Macedonian Cup - Main |
| Semi-finals - 2nd leg | Milano Kumanovo | Makedonija GP | 1:0 | details | 06.05.2009 |
North Macedonia: First League - Main |
| 29. Round | Milano Kumanovo | Vardar | 1:0 | details | 03.05.2009 |
| 28. Round | Rabotnicki | Milano Kumanovo | 2:0 | details | 29.04.2009 |
| 27. Round | Milano Kumanovo | Turnovo | 1:2 | details | 26.04.2009 |
| 25. Round | Milano Kumanovo | Pelister | 4:1 | details | 18.04.2009 |
| 24. Round | Napredok | Milano Kumanovo | 1:1 | details | 12.04.2009 |
North Macedonia: Macedonian Cup - Main |
| Semi-finals - 1st leg | Makedonija GP | Milano Kumanovo | 2:0 | details | 08.04.2009 |
North Macedonia: First League - Main |
| 23. Round | Milano Kumanovo | Pobeda | 3:1 | details | 04.04.2009 |
| 22. Round | Milano Kumanovo | Rabotnicki | 1:0 | details | 23.03.2009 |