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| Date | Match | Score |
|---|---|---|
| 09.05.2026 | Pelister - Shkupi 1927 | 7 : 0 |
| 25.11.2025 | Shkupi 1927 - Pelister | 0 : 3 |
| 25.08.2025 | Pelister - Shkupi 1927 | 2 : 0 |
| 15.03.2025 | Shkupi 1927 - Pelister | 0 : 1 |
| 02.03.2025 | Shkupi 1927 - Pelister | 3 : 1 |
| 20.10.2024 | Pelister - Shkupi 1927 | 0 : 0 |
| 16.04.2022 | Pelister - Shkupi 1927 | 0 : 1 |
| 21.11.2021 | Shkupi 1927 - Pelister | 5 : 0 |
| 18.08.2021 | Pelister - Shkupi 1927 | 0 : 2 |
| 09.05.2021 | Shkupi 1927 - Pelister | 0 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 06.09.2026 | Pelister - FK Rabotnicki | 2 - 0 | W |
| 02.09.2026 | Studenicani - Pelister | 1 - 6 | W |
| 29.08.2026 | Makedonija GjP - Pelister | 0 - 1 | W |
| 22.08.2026 | Pelister - Akademija Pandev | 0 - 0 | D |
| 16.08.2026 | Pelister - Kamjani | 1 - 1 | D |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.09.2026 | Sasa - Shkupi 1927 | 1 - 0 | L |
| 05.09.2026 | Gorno Lisiče - Shkupi 1927 | 4 - 0 | L |
| 30.08.2026 | Shkupi 1927 - Teteks | 1 - 3 | L |
| 22.08.2026 | Kozuv Gevgelija - Shkupi 1927 | 2 - 0 | L |
| 15.08.2026 | Shkupi 1927 - Detonit Plachkovica | 0 - 2 | L |