| 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 |
| 2016-12-13 | ForfarvAnnan AthleticLeague Two · Scotland | 5–1 | League Two · Scotland |
| 2016-12-10 | Annan AthleticvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2016-11-19 | Annan AthleticvElginLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2016-11-12 | Edinburgh CityvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2016-11-08 | Annan AthleticvMontroseLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2016-11-05 | Annan AthleticvArbroathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2016-10-15 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2016-10-01 | ElginvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2016-09-24 | Annan AthleticvEdinburgh CityLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2016-09-17 | ArbroathvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2016-09-10 | Annan AthleticvForfarLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2016-08-27 | MontrosevAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2016-08-20 | Annan AthleticvClydeLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2016-08-13 | BerwickvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2016-08-06 | Annan AthleticvStirlingLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2016-04-30 | Annan AthleticvQueens ParkLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2016-04-23 | StirlingvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2016-04-16 | Annan AthleticvEast StirlingLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2016-04-09 | Annan AthleticvArbroathLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2016-04-02 | ElginvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2016-03-26 | MontrosevAnnan AthleticLeague Two · Scotland | 0–5 | League Two · Scotland |
| 2016-03-22 | ClydevAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2016-03-19 | Annan AthleticvBerwickLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2016-03-15 | Queens ParkvAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2016-03-12 | East FifevAnnan AthleticLeague Two · Scotland | 4–2 | League Two · Scotland |
| 2016-03-05 | Annan AthleticvClydeLeague Two · Scotland | 3–3 | League Two · Scotland |
| 2016-02-27 | Annan AthleticvStirlingLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2016-02-20 | East StirlingvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |