| 24/05/2026 |   Akademija Pandev vs Shkupi 1927 | 6 - 0 | First League
Phase : J33 | 2025 | Stadion Blagoj Istatov |
| 16/05/2026 |  Shkupi 1927 vs FK Rabotnicki | 0 - 7 | First League
Phase : J32 | 2025 | - |
| 09/05/2026 |  Pelister vs Shkupi 1927 | 7 - 0 | First League
Phase : J31 | 2025 | - |
| 01/05/2026 |  Shkupi 1927 vs Makedonija GjP | 0 - 4 | First League
Phase : J30 | 2025 | - |
| 24/04/2026 |  Aresimi vs Shkupi 1927 | 5 - 1 | First League
Phase : J29 | 2025 | Igralište Golema Rečica |
| 18/04/2026 |  Shkupi 1927 vs Vardar Skopje | 0 - 7 | First League
Phase : J28 | 2025 | - |
| 13/04/2026 |  Shkendija vs Shkupi 1927 | 6 - 0 | First League
Phase : J27 | 2025 | - |
| 09/04/2026 |  Shkupi 1927 vs Struga | 0 - 3 | First League
Phase : J26 | 2025 | - |
| 03/04/2026 |  Sileks vs Shkupi 1927 | 6 - 0 | First League
Phase : J25 | 2025 | - |
| 23/03/2026 |  Shkupi 1927 vs Bashkimi Kumanovo | 2 - 3 | First League
Phase : J24 | 2025 | - |
| 15/03/2026 |  Tikveš vs Shkupi 1927 | 6 - 0 | First League
Phase : J23 | 2025 | - |
| 07/03/2026 | Struga vs Shkupi 1927 | 5 - 0 | First League
Phase : J22 | 2025 | Stade Gradska Plaža |
| 03/03/2026 | Shkupi 1927 vs Bashkimi Kumanovo | 0 - 2 | First League
Phase : J21 | 2025 | Stadion Čair |
| 28/02/2026 | FK Rabotnicki vs Shkupi 1927 | 3 - 0 | First League
Phase : J20 | 2025 | Arène Toše Proeski |
| 22/02/2026 | Shkupi 1927 vs Aresimi | 0 - 3 | First League
Phase : J19 | 2025 | Stadion Čair |
| 16/02/2026 | Makedonija GjP vs Shkupi 1927 | 3 - 0 | First League
Phase : J18 | 2025 | Stadion Gorče Petrov |
| 10/02/2026 | Shkupi 1927 vs Tikveš | 0 - 6 | First League
Phase : J17 | 2025 | Stadion Cair |
| 04/02/2026 | Aresimi vs Shkupi 1927 | 1 - 0 | Friendlies Clubs
Phase : Club Friendly | 2026 | Igralište Golema Rečica |
| 24/01/2026 | Makedonija GjP vs Shkupi 1927 | 0 - 0 | Friendlies Clubs
Phase : Club Friendly | 2026 | - |
| 18/01/2026 | FK Rabotnicki vs Shkupi 1927 | 5 - 2 | Friendlies Clubs
Phase : Club Friendly | 2026 | - |
| 07/12/2025 | Shkupi 1927 vs Akademija Pandev | 1 - 3 | First League
Phase : J16 | 2025 | Stadion Čair |
| 30/11/2025 | Vardar Skopje vs Shkupi 1927 | 6 - 1 | First League
Phase : J15 | 2025 | Arène Toše Proeski |
| 25/11/2025 | Shkupi 1927 vs Pelister | 0 - 3 | First League
Phase : J14 | 2025 | Stadion Cair |
| 15/11/2025 | Shkupi 1927 vs Shkendija | 1 - 2 | First League
Phase : J12 | 2025 | Stadion Čair |
| 10/11/2025 | Sileks vs Shkupi 1927 | 5 - 1 | First League
Phase : J13 | 2025 | Gradski stadion Kratovo |
| 30/10/2025 | Shkupi 1927 vs Struga | 1 - 2 | First League
Phase : J11 | 2025 | Stadion Čair |
| 24/10/2025 | Bashkimi Kumanovo vs Shkupi 1927 | 4 - 1 | First League
Phase : J10 | 2025 | Stadion FK Bashkimi |
| 04/10/2025 | Shkupi 1927 vs FK Rabotnicki | 1 - 1 | First League
Phase : J9 | 2025 | Stadion Čair |
| 27/09/2025 | Aresimi vs Shkupi 1927 | 4 - 2 | First League
Phase : J8 | 2025 | Stadion Čegrane |
| 24/09/2025 |  Ohrid vs Shkupi 1927 | 3 - 0 | Coupe
Phase : 8e de finale | 2025 | - |
| 20/09/2025 | Shkupi 1927 vs Makedonija GjP | 0 - 2 | First League
Phase : J7 | 2025 | Stadion Čair |
| 17/09/2025 | Tikveš vs Shkupi 1927 | 1 - 0 | First League
Phase : J6 | 2025 | Gradski Stadion |
| 13/09/2025 | Akademija Pandev vs Shkupi 1927 | 1 - 0 | First League
Phase : J5 | 2025 | Stadion Blagoj Istatov |
| 10/09/2025 |  Kozuv Gevgelija vs Shkupi 1927 | 0 - 2 | Coupe
Phase : 16e de finale | 2025 | Stadion FK Kožuf |
| 29/08/2025 | Shkupi 1927 vs Vardar Skopje | 2 - 4 | First League
Phase : J4 | 2025 | Stadion Blagoj Istatov |
| 25/08/2025 | Pelister vs Shkupi 1927 | 2 - 0 | First League
Phase : J3 | 2025 | Gradski Stadion |
| 08/08/2025 | Shkendija vs Shkupi 1927 | 5 - 1 | First League
Phase : J1 | 2025 | Arène Ecolog |
| 12/05/2025 |  Shkupi 1927 vs Shkëndija Haraçinë | 1 - 6 | Friendlies Clubs
Phase : Club Friendlies 5 | 2025 | - |
| 11/05/2025 | Shkupi 1927 vs Tikveš | 1 - 1 | First League
Phase : J32 | 2024 | Stadion Čair |
| 07/05/2025 | Akademija Pandev vs Shkupi 1927 | 4 - 3 | First League
Phase : J31 | 2024 | Stadion Blagoj Istatov |
| 03/05/2025 | Shkupi 1927 vs Vardar Skopje | 0 - 2 | First League
Phase : J30 | 2024 | Stadion Čair |
| 27/04/2025 | Shkendija vs Shkupi 1927 | 3 - 3 | First League
Phase : J29 | 2024 | Arène Ecolog |
| 19/04/2025 | Shkupi 1927 vs Sileks | 1 - 2 | First League
Phase : J28 | 2024 | Stadion Čair |
| 13/04/2025 |  KF Gostivari vs Shkupi 1927 | 3 - 1 | First League
Phase : J27 | 2024 | Stadion Boris Trajkovski |
| 06/04/2025 | Shkupi 1927 vs FK Rabotnicki | 0 - 0 | First League
Phase : J26 | 2024 | Stadion Čair |
| 31/03/2025 | Struga vs Shkupi 1927 | 0 - 0 | First League
Phase : J25 | 2024 | Stade Gradska Plaža |
| 15/03/2025 | Shkupi 1927 vs Pelister | 0 - 1 | First League
Phase : J24 | 2024 | Stadion Čair |
| 09/03/2025 |  Shkupi 1927 vs Besa Dobërdoll | 2 - 3 | First League
Phase : J23 | 2024 | Stadion Čair |
| 05/03/2025 | Tikveš vs Shkupi 1927 | 1 - 0 | First League
Phase : J22 | 2024 | Gradski Stadion |
| 02/03/2025 | Shkupi 1927 vs Pelister | 3 - 1 | First League
Phase : J21 | 2024 | Stadion Čair |
