| 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 |