| 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 |