| 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 |
| 2021-09-25 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2021-09-18 | ElginvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2021-09-11 | Annan AthleticvStenhousemuirLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2021-08-28 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2021-08-21 | Albion RvsvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2021-08-14 | Annan AthleticvStirlingLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2021-08-07 | StranraervAnnan AthleticLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2021-07-31 | Annan AthleticvForfarLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2021-05-01 | Annan AthleticvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-04-29 | BrechinvAnnan AthleticLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2021-04-27 | Annan AthleticvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-04-24 | Albion RvsvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-04-20 | Annan AthleticvStenhousemuirLeague Two · Scotland | 5–1 | League Two · Scotland |
| 2021-04-17 | Annan AthleticvBrechinLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2021-04-13 | Queens ParkvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-04-10 | Annan AthleticvStirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2021-04-06 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-04-03 | Annan AthleticvElginLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2021-03-27 | Albion RvsvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-03-20 | Annan AthleticvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2021-01-02 | StranraervAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2020-12-22 | BrechinvAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2020-12-19 | Annan AthleticvQueens ParkLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2020-12-05 | ElginvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2020-11-28 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 0–4 | League Two · Scotland |
| 2020-11-21 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2020-11-07 | Annan AthleticvAlbion RvsLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2020-10-31 | StirlingvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |