| 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 |
| 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 |