| 2018-12-08 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2018-12-01 | PeterheadvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2018-11-17 | Annan AthleticvStirlingLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2018-11-10 | Annan AthleticvCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2018-11-03 | Queens ParkvAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2018-10-27 | ElginvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2018-10-06 | Annan AthleticvAlbion RvsLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2018-09-29 | Annan AthleticvPeterheadLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2018-09-22 | StirlingvAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2018-09-15 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2018-09-01 | Annan AthleticvClydeLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2018-08-25 | BerwickvAnnan AthleticLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2018-08-18 | Annan AthleticvQueens ParkLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2018-08-11 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2018-08-04 | Annan AthleticvElginLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2018-04-28 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2018-04-21 | Annan AthleticvStirlingLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2018-04-14 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2018-04-07 | Annan AthleticvElginLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2018-03-31 | Annan AthleticvBerwickLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2018-03-24 | PeterheadvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2018-03-17 | Annan AthleticvClydeLeague Two · Scotland | 1–1 | League Two · Scotland |
| 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 |