| 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 |
| 2025-05-03 | Annan AthleticvCove RangersLeague One · Scotland | 2–4 | League One · Scotland |
| 2025-04-26 | DumbartonvAnnan AthleticLeague One · Scotland | 3–1 | League One · Scotland |
| 2025-04-19 | Annan AthleticvArbroathLeague One · Scotland | 5–1 | League One · Scotland |
| 2025-04-12 | AlloavAnnan AthleticLeague One · Scotland | 1–0 | League One · Scotland |
| 2025-04-05 | Annan AthleticvQueen of SthLeague One · Scotland | 0–2 | League One · Scotland |
| 2025-03-29 | Annan AthleticvKelty HeartsLeague One · Scotland | 2–1 | League One · Scotland |
| 2025-03-22 | MontrosevAnnan AthleticLeague One · Scotland | 3–1 | League One · Scotland |
| 2025-03-15 | Inverness CvAnnan AthleticLeague One · Scotland | 0–1 | League One · Scotland |
| 2025-03-08 | Annan AthleticvStenhousemuirLeague One · Scotland | 0–2 | League One · Scotland |
| 2025-03-01 | ArbroathvAnnan AthleticLeague One · Scotland | 3–0 | League One · Scotland |
| 2025-02-22 | Annan AthleticvAlloaLeague One · Scotland | 3–4 | League One · Scotland |
| 2025-02-15 | Cove RangersvAnnan AthleticLeague One · Scotland | 3–1 | League One · Scotland |
| 2025-02-08 | Annan AthleticvDumbartonLeague One · Scotland | 2–1 | League One · Scotland |
| 2025-02-01 | Kelty HeartsvAnnan AthleticLeague One · Scotland | 1–3 | League One · Scotland |
| 2025-01-25 | Annan AthleticvMontroseLeague One · Scotland | 2–2 | League One · Scotland |
| 2025-01-18 | Annan AthleticvInverness CLeague One · Scotland | 0–3 | League One · Scotland |
| 2025-01-04 | StenhousemuirvAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |