| 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 |
| 2022-03-19 | StirlingvAnnan AthleticLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2022-03-12 | Annan AthleticvElginLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2022-03-05 | Annan AthleticvStranraerLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2022-03-02 | Albion RvsvAnnan AthleticLeague Two · Scotland | 1–4 | League Two · Scotland |
| 2022-02-26 | Kelty HeartsvAnnan AthleticLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2022-02-19 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2022-02-15 | ElginvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2022-02-05 | Annan AthleticvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2022-01-29 | Annan AthleticvStirlingLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2022-01-15 | Annan AthleticvForfarLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2022-01-08 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2022-01-02 | StranraervAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-12-26 | Annan AthleticvKelty HeartsLeague Two · Scotland | 5–1 | League Two · Scotland |
| 2021-12-18 | StirlingvAnnan AthleticLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2021-12-11 | Annan AthleticvElginLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2021-12-03 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2021-11-20 | Annan AthleticvAlbion RvsLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-11-13 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2021-11-06 | Annan AthleticvStranraerLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2021-10-30 | Annan AthleticvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-10-16 | ForfarvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2021-10-02 | Kelty HeartsvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |