| 2023-09-29 | HamiltonvAnnan AthleticLeague One · Scotland | 5–0 | League One · Scotland |
| 2023-09-23 | Annan AthleticvAlloaLeague One · Scotland | 1–1 | League One · Scotland |
| 2023-09-16 | Annan AthleticvStirlingLeague One · Scotland | 3–0 | League One · Scotland |
| 2023-09-02 | Kelty HeartsvAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2023-08-26 | Annan AthleticvEdinburgh CityLeague One · Scotland | 3–2 | League One · Scotland |
| 2023-08-19 | Queen of SthvAnnan AthleticLeague One · Scotland | 3–1 | League One · Scotland |
| 2023-08-12 | Annan AthleticvMontroseLeague One · Scotland | 1–3 | League One · Scotland |
| 2023-08-05 | FalkirkvAnnan AthleticLeague One · Scotland | 3–0 | League One · 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 |
| 2023-01-28 | Annan AthleticvEast FifeLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2023-01-21 | Annan AthleticvBonnyrigg RoseLeague Two · Scotland | 4–0 | League Two · Scotland |
| 2023-01-14 | ElginvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2023-01-07 | Annan AthleticvForfarLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2022-12-23 | Annan AthleticvAlbion RvsLeague Two · Scotland | 5–1 | League Two · Scotland |
| 2022-12-03 | East FifevAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2022-11-26 | StranraervAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2022-11-19 | Annan AthleticvElginLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2022-11-12 | StirlingvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2022-11-05 | ForfarvAnnan AthleticLeague Two · Scotland | 1–4 | League Two · Scotland |
| 2022-10-29 | Annan AthleticvDumbartonLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2022-10-15 | Annan AthleticvStranraerLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2022-10-11 | Bonnyrigg RosevAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2022-10-08 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2022-10-01 | ElginvAnnan AthleticLeague Two · Scotland | 5–1 | League Two · Scotland |
| 2022-09-17 | Annan AthleticvEast FifeLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2022-09-03 | Annan AthleticvForfarLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2022-08-27 | Albion RvsvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2022-08-20 | Annan AthleticvStirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2022-08-13 | DumbartonvAnnan AthleticLeague Two · Scotland | 4–0 | League Two · Scotland |
| 2022-08-06 | Annan AthleticvStenhousemuirLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2022-07-30 | StranraervAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2022-04-30 | Annan AthleticvKelty HeartsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2022-04-22 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2022-04-16 | ForfarvAnnan AthleticLeague Two · Scotland | 5–1 | League Two · Scotland |
| 2022-04-09 | Annan AthleticvCowdenbeathLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2022-04-02 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2022-03-26 | Annan AthleticvAlbion RvsLeague Two · Scotland | 2–4 | League Two · Scotland |