| 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 |
| 2024-12-28 | Queen of SthvAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-12-21 | Annan AthleticvArbroathLeague One · Scotland | 0–4 | League One · Scotland |
| 2024-12-14 | DumbartonvAnnan AthleticLeague One · Scotland | 1–5 | League One · Scotland |
| 2024-12-07 | Annan AthleticvCove RangersLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-11-23 | MontrosevAnnan AthleticLeague One · Scotland | 2–1 | League One · Scotland |
| 2024-11-16 | Annan AthleticvKelty HeartsLeague One · Scotland | 0–2 | League One · Scotland |
| 2024-11-09 | Annan AthleticvStenhousemuirLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-11-02 | AlloavAnnan AthleticLeague One · Scotland | 5–0 | League One · Scotland |
| 2024-10-26 | Annan AthleticvQueen of SthLeague One · Scotland | 1–0 | League One · Scotland |
| 2024-10-19 | Inverness CvAnnan AthleticLeague One · Scotland | 1–0 | League One · Scotland |
| 2024-10-05 | Annan AthleticvMontroseLeague One · Scotland | 1–0 | League One · Scotland |
| 2024-09-28 | Kelty HeartsvAnnan AthleticLeague One · Scotland | 3–0 | League One · Scotland |
| 2024-09-21 | ArbroathvAnnan AthleticLeague One · Scotland | 2–0 | League One · Scotland |
| 2024-09-14 | Annan AthleticvDumbartonLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-08-31 | StenhousemuirvAnnan AthleticLeague One · Scotland | 5–1 | League One · Scotland |
| 2024-08-24 | Annan AthleticvAlloaLeague One · Scotland | 0–1 | League One · Scotland |
| 2024-08-17 | Queen of SthvAnnan AthleticLeague One · Scotland | 2–0 | League One · Scotland |
| 2024-08-10 | Annan AthleticvInverness CLeague One · Scotland | 1–0 | League One · Scotland |
| 2024-08-03 | Cove RangersvAnnan AthleticLeague One · Scotland | 1–3 | League One · Scotland |
| 2024-05-04 | StirlingvAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-04-27 | Annan AthleticvFalkirkLeague One · Scotland | 3–3 | League One · Scotland |
| 2024-04-20 | Edinburgh CityvAnnan AthleticLeague One · Scotland | 1–2 | League One · Scotland |
| 2024-04-13 | Annan AthleticvCove RangersLeague One · Scotland | 4–2 | League One · Scotland |
| 2024-04-06 | Annan AthleticvHamiltonLeague One · Scotland | 1–3 | League One · Scotland |
| 2024-03-30 | AlloavAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-03-23 | Annan AthleticvKelty HeartsLeague One · Scotland | 3–2 | League One · Scotland |
| 2024-03-16 | MontrosevAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-03-09 | Annan AthleticvQueen of SthLeague One · Scotland | 2–1 | League One · Scotland |
| 2024-03-02 | FalkirkvAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-02-24 | Cove RangersvAnnan AthleticLeague One · Scotland | 2–1 | League One · Scotland |
| 2024-02-17 | Annan AthleticvStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 2024-02-13 | AlloavAnnan AthleticLeague One · Scotland | 2–1 | League One · Scotland |
| 2024-02-10 | HamiltonvAnnan AthleticLeague One · Scotland | 2–3 | League One · Scotland |
| 2024-02-03 | Annan AthleticvAlloaLeague One · Scotland | 2–3 | League One · Scotland |
| 2024-01-27 | Annan AthleticvEdinburgh CityLeague One · Scotland | 3–0 | League One · Scotland |
| 2024-01-13 | Kelty HeartsvAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2024-01-06 | Annan AthleticvMontroseLeague One · Scotland | 2–2 | League One · Scotland |
| 2023-12-30 | Queen of SthvAnnan AthleticLeague One · Scotland | 2–1 | League One · Scotland |
| 2023-12-23 | Annan AthleticvFalkirkLeague One · Scotland | 0–3 | League One · Scotland |
| 2023-12-16 | StirlingvAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2023-12-09 | Annan AthleticvCove RangersLeague One · Scotland | 1–3 | League One · Scotland |
| 2023-11-28 | Annan AthleticvHamiltonLeague One · Scotland | 1–2 | League One · Scotland |
| 2023-11-11 | MontrosevAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2023-11-04 | Annan AthleticvKelty HeartsLeague One · Scotland | 2–2 | League One · Scotland |
| 2023-10-28 | Edinburgh CityvAnnan AthleticLeague One · Scotland | 3–2 | League One · Scotland |
| 2023-10-21 | Annan AthleticvQueen of SthLeague One · Scotland | 0–1 | League One · Scotland |
| 2023-10-07 | Cove RangersvAnnan AthleticLeague One · Scotland | 3–2 | League One · Scotland |