| 25/07/2026 |   Vardar Skopje vs Bregalnica Štip | 16h00 | First League
Phase : J1 | 2026 | - |
| 08/08/2026 |  Bregalnica Štip vs Aresimi | 16h00 | First League
Phase : J2 | 2026 | Gradski Stadion |
| 15/08/2026 |  Shkendija vs Bregalnica Štip | 16h00 | First League
Phase : J3 | 2026 | - |
| 22/08/2026 |  Bregalnica Štip vs Bashkimi Kumanovo | 16h00 | First League
Phase : J4 | 2026 | Gradski Stadion |
| 29/08/2026 |  Struga vs Bregalnica Štip | 16h00 | First League
Phase : J5 | 2026 | - |
| 05/09/2026 |  Bregalnica Štip vs Shkëndija Haraçinë | 16h00 | First League
Phase : J6 | 2026 | Gradski Stadion |
| 12/09/2026 |  Sileks vs Bregalnica Štip | 16h00 | First League
Phase : J7 | 2026 | - |
| 19/09/2026 |  Bregalnica Štip vs Skopje | 16h00 | First League
Phase : J8 | 2026 | Gradski Stadion |
| 09/10/2026 |  Tikveš vs Bregalnica Štip | 16h00 | First League
Phase : J9 | 2026 | - |
| 17/10/2026 | Bregalnica Štip vs Vardar Skopje | 16h00 | First League
Phase : J10 | 2026 | Gradski Stadion |
| 24/10/2026 | Aresimi vs Bregalnica Štip | 16h00 | First League
Phase : J11 | 2026 | Igralište Golema Rečica |
| 31/10/2026 | Bregalnica Štip vs Shkendija | 17h00 | First League
Phase : J12 | 2026 | Gradski Stadion |
| 07/11/2026 | Bashkimi Kumanovo vs Bregalnica Štip | 17h00 | First League
Phase : J13 | 2026 | Stadion FK Bashkimi |
| 21/11/2026 | Bregalnica Štip vs Struga | 17h00 | First League
Phase : J14 | 2026 | Gradski Stadion |
| 28/11/2026 | Shkëndija Haraçinë vs Bregalnica Štip | 17h00 | First League
Phase : J15 | 2026 | - |
| 01/12/2026 | Bregalnica Štip vs Sileks | 17h00 | First League
Phase : J16 | 2026 | Gradski Stadion |
| 05/12/2026 | Skopje vs Bregalnica Štip | 17h00 | First League
Phase : J17 | 2026 | - |
| 12/12/2026 | Bregalnica Štip vs Tikveš | 17h00 | First League
Phase : J18 | 2026 | Gradski Stadion |
