| 2018-03-13 | MontrosevAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2018-03-10 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2018-02-24 | Annan AthleticvStenhousemuirLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2018-02-20 | Annan AthleticvPeterheadLeague Two · Scotland | 3–3 | League Two · Scotland |
| 2018-02-17 | StirlingvAnnan AthleticLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2018-02-10 | ElginvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2018-02-03 | Annan AthleticvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2018-01-27 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2018-01-13 | BerwickvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2018-01-06 | Annan AthleticvMontroseLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2018-01-02 | ClydevAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2017-12-23 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2017-12-16 | Annan AthleticvStirlingLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2017-12-09 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2017-12-02 | Annan AthleticvElginLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2017-11-25 | Annan AthleticvClydeLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2017-11-18 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2017-11-11 | MontrosevAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2017-11-04 | Annan AthleticvBerwickLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2017-10-28 | PeterheadvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2017-10-21 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2017-09-30 | Annan AthleticvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2017-09-23 | StirlingvAnnan AthleticLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2017-09-16 | Annan AthleticvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2017-09-09 | ElginvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2017-08-26 | Annan AthleticvMontroseLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2017-08-19 | BerwickvAnnan AthleticLeague Two · Scotland | 1–5 | League Two · Scotland |
| 2017-08-12 | ClydevAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2017-08-05 | Annan AthleticvPeterheadLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2017-05-06 | ForfarvAnnan AthleticLeague Two · Scotland | 2–4 | League Two · Scotland |
| 2017-04-29 | Annan AthleticvMontroseLeague Two · Scotland | 5–1 | League Two · Scotland |
| 2017-04-22 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2017-04-15 | Annan AthleticvBerwickLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2017-04-08 | ClydevAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2017-04-01 | Annan AthleticvArbroathLeague Two · Scotland | 2–5 | League Two · Scotland |
| 2017-03-25 | Annan AthleticvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2017-03-18 | StirlingvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2017-03-11 | Annan AthleticvElginLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2017-03-04 | MontrosevAnnan AthleticLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2017-02-25 | Annan AthleticvClydeLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2017-02-18 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2017-02-11 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2017-02-04 | BerwickvAnnan AthleticLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2017-01-28 | Annan AthleticvStirlingLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2017-01-21 | ArbroathvAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2017-01-14 | ElginvAnnan AthleticLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2017-01-07 | Annan AthleticvForfarLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2016-12-31 | ClydevAnnan AthleticLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2016-12-24 | Annan AthleticvBerwickLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2016-12-17 | StirlingvAnnan AthleticLeague Two · Scotland | 3–1 | League Two · Scotland |