| 2026-05-02 | Annan AthleticvForfarLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2026-04-25 | ClydevAnnan AthleticLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2026-04-18 | Annan AthleticvSpartansLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2026-04-11 | ElginvAnnan AthleticLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2026-04-04 | East KilbridevAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2026-03-28 | Annan AthleticvStranraerLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2026-03-21 | DumbartonvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2026-03-14 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2026-03-10 | Annan AthleticvElginLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2026-03-07 | Annan AthleticvStirlingLeague Two · Scotland | 3–3 | League Two · Scotland |
| 2026-02-28 | SpartansvAnnan AthleticLeague Two · Scotland | 4–0 | League Two · Scotland |
| 2026-02-24 | StirlingvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2026-02-21 | ForfarvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2026-02-14 | Annan AthleticvEast KilbrideLeague Two · Scotland | 2–4 | League Two · Scotland |
| 2026-02-10 | Annan AthleticvDumbartonLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2026-02-07 | StranraervAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2026-01-31 | Annan AthleticvClydeLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2026-01-24 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |