Home History
| North Macedonia Second League | 2023/08/26 14:00 | FK Kozuf Gevgelija v FK Skopje | L | 4-2 |
| North Macedonia Second League | 2023/08/20 15:00 | FK Skopje v Detonit Plackovica | L | 1-4 |
| North Macedonia Second League | 2023/08/12 15:00 | FK Sasa v FK Skopje | D | 1-1 |
| Europe Friendlies | 2023/07/27 16:12 | FK Skopje v FK Gostivar | L | 2-4 |
| North Macedonia Play-Offs | 2023/05/21 15:00 | FK Skopje v Vardar Skopje | L | 0-3 |
| North Macedonia First League | 2023/05/14 15:00 | FK Skopje v Bregalnica Stip | L | 1-2 |
| North Macedonia First League | 2023/05/10 15:00 | Tikves Kavadarci v FK Skopje | L | 4-0 |
| North Macedonia First League | 2023/04/30 14:00 | FK Pobeda v FK Skopje | W | 0-4 |
Away History
| North Macedonia Second League | 2023/08/30 14:00 | Ohrid v FK Karaorman | L | 1-0 |
| North Macedonia Second League | 2023/08/26 14:00 | FK Karaorman v FK Vardar Negotino | W | 2-0 |
| North Macedonia Second League | 2023/08/12 15:00 | FK Kozuf Gevgelija v FK Karaorman | L | 3-0 |
| North Macedonia Second League | 2023/05/13 15:00 | FK Karaorman v FK Gostivar | L | 0-2 |
| North Macedonia Second League | 2023/05/09 15:00 | KF Besa Doberdoll v FK Karaorman | L | 1-0 |
| North Macedonia Second League | 2023/05/06 15:00 | FK Karaorman v FK Sasa | L | 1-2 |
| North Macedonia Second League | 2023/04/29 14:00 | FK Lokomotive v FK Karaorman | L | 3-0 |
| North Macedonia Second League | 2023/04/26 14:00 | Pelister Bitola v FK Karaorman | L | 2-0 |
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