| 2024-03-03 14:00 | SP21 | Shkupi 1927 |  | 0-0 |  | GFK Tikves | ||
| 2024-02-18 14:00 | SP19 | Shkupi 1927 | | 3-0 |  | Voska Sport | Erik Gronner 5' 50', Kristijan Trapanovski 45' | |
| 2023-12-03 13:00 | SP17 | Shkupi 1927 | | 1-0 |  | KF Shkendija 79 | Kristijan Trapanovski 38' | |
| 2023-11-26 13:00 | SP15 | Shkupi 1927 | | 1-0 |  | Makedonija GP | Mario Mladenovski 67' | |
| 2023-11-05 13:00 | SP13 | Shkupi 1927 | | 2-0 |  | Vardar | Arbin Vosha 25', Issah Kuka 74' | |
| 2023-10-29 13:00 | SP12 | Shkupi 1927 | | 3-0 |  | Rabotnicki | Queven 41' 74', Issah Kuka 52' | |
| 2023-10-22 14:00 | SP11 | Shkupi 1927 | | 1-0 |  | FK Bregalnica | Darko Ilieski 5' | |
| 2023-10-01 14:00 | SP9 | Shkupi 1927 | | 2-0 |  | FK Struga | Queven 52', Arbin Vosha 90' | |
| 2023-09-16 15:00 | SP7 | Shkupi 1927 | | 1-0 |  | Brera Strumica | Luan Abazi 69' | |
| 2023-08-27 16:00 | SP5 | Shkupi 1927 | | 3-1 |  | KF Gostivari | Armin Hodzic 27' (S), Suad Sahiti 70', Arbin Vosha 90'; Alper Potuk 64' | |
| 2023-08-20 17:00 | SP3 | Shkupi 1927 | | 1-1 |  | Sileks FC | Michal Pintér 45'; Marko Gjorgjievski 76' | |
| 2023-07-20 21:00 | 1VR | Shkupi 1927 | | 0-0 |  | FC Hegelmann |
