| 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 |
| 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 |
| 2023-05-06 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2023-04-29 | Annan AthleticvBonnyrigg RoseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2023-04-22 | StirlingvAnnan AthleticLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2023-04-15 | Annan AthleticvAlbion RvsLeague Two · Scotland | 4–0 | League Two · Scotland |
| 2023-04-08 | Annan AthleticvDumbartonLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2023-04-01 | East FifevAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2023-03-25 | Annan AthleticvStranraerLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2023-03-18 | ForfarvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2023-03-11 | Annan AthleticvElginLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2023-03-04 | Annan AthleticvStenhousemuirLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2023-02-25 | Albion RvsvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2023-02-18 | Annan AthleticvStirlingLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2023-02-11 | DumbartonvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2023-02-04 | Bonnyrigg RosevAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |