| 2025-12-27 | Annan AthleticvStranraerLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2025-12-20 | East KilbridevAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2025-12-13 | Annan AthleticvForfarLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2025-12-06 | Annan AthleticvSpartansLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2025-11-22 | ClydevAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2025-11-15 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2025-11-08 | DumbartonvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2025-11-01 | ElginvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2025-10-18 | Annan AthleticvStirlingLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2025-10-04 | StranraervAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2025-09-27 | Annan AthleticvEast KilbrideLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2025-09-20 | ForfarvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2025-09-13 | Annan AthleticvClydeLeague Two · Scotland | 0–6 | League Two · Scotland |
| 2025-08-30 | SpartansvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2025-08-23 | Annan AthleticvDumbartonLeague Two · Scotland | 3–4 | League Two · Scotland |
| 2025-08-16 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2025-08-09 | StirlingvAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2025-08-02 | Annan AthleticvElginLeague Two · Scotland | 3–2 | League Two · Scotland |