| 2014-10-21 | Annan AthleticvArbroathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2014-10-18 | East FifevAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2014-09-27 | ClydevAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2014-09-20 | East StirlingvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2014-09-13 | Annan AthleticvBerwickLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2014-08-30 | Annan AthleticvElginLeague Two · Scotland | 3–3 | League Two · Scotland |
| 2014-08-23 | MontrosevAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2014-08-16 | Annan AthleticvQueens ParkLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2014-08-09 | Albion RvsvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2014-05-03 | Annan AthleticvElginLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2014-04-26 | MontrosevAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2014-04-19 | Annan AthleticvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2014-04-12 | East StirlingvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2014-04-05 | ClydevAnnan AthleticLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2014-03-29 | Annan AthleticvStirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2014-03-25 | Albion RvsvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2014-03-22 | Annan AthleticvPeterheadLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2014-03-15 | ElginvAnnan AthleticLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2014-03-04 | PeterheadvAnnan AthleticLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2014-03-01 | Annan AthleticvBerwickLeague Two · Scotland | 4–0 | League Two · Scotland |
| 2014-02-25 | Annan AthleticvQueens ParkLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2014-02-22 | Queens ParkvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2014-02-15 | Annan AthleticvEast StirlingLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2014-02-08 | Annan AthleticvMontroseLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2014-01-25 | StirlingvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2014-01-18 | Annan AthleticvClydeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2014-01-11 | BerwickvAnnan AthleticLeague Two · Scotland | 1–4 | League Two · Scotland |
| 2014-01-04 | Annan AthleticvAlbion RvsLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2013-12-28 | Annan AthleticvElginLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2013-12-26 | MontrosevAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2013-12-07 | East StirlingvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2013-12-03 | ClydevAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2013-11-23 | Annan AthleticvStirlingLeague Two · Scotland | 4–4 | League Two · Scotland |
| 2013-11-16 | Annan AthleticvBerwickLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2013-11-09 | Albion RvsvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2013-11-05 | Annan AthleticvPeterheadLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2013-10-29 | Annan AthleticvEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2013-10-26 | ElginvAnnan AthleticLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2013-09-28 | Queens ParkvAnnan AthleticLeague Two · Scotland | 2–5 | League Two · Scotland |
| 2013-09-21 | Annan AthleticvClydeLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2013-09-14 | StirlingvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2013-08-31 | BerwickvAnnan AthleticLeague Two · Scotland | 4–2 | League Two · Scotland |
| 2013-08-24 | Annan AthleticvAlbion RvsLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2013-08-17 | Annan AthleticvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2013-08-10 | PeterheadvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2013-05-04 | Annan AthleticvMontroseLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2013-04-27 | BerwickvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2013-04-20 | Annan AthleticvStirlingLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2013-04-13 | East StirlingvAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2013-04-10 | Annan AthleticvQueens ParkLeague Two · Scotland | 2–0 | League Two · Scotland |