| 2010-08-21 | Annan AthleticvStranraerLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2010-08-14 | ArbroathvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2010-08-07 | Annan AthleticvEast StirlingLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2010-05-01 | Annan AthleticvBerwickLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2010-04-24 | East StirlingvAnnan AthleticLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2010-04-17 | Annan AthleticvStranraerLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2010-04-13 | Annan AthleticvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2010-04-10 | MontrosevAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2010-04-06 | ElginvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2010-04-03 | Annan AthleticvLivingstonLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2010-03-27 | Albion RvsvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2010-03-24 | StranraervAnnan AthleticLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2010-03-20 | Annan AthleticvQueens ParkLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2010-03-16 | Annan AthleticvLivingstonLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2010-03-13 | ForfarvAnnan AthleticLeague Two · Scotland | 1–5 | League Two · Scotland |
| 2010-03-06 | Annan AthleticvElginLeague Two · Scotland | 3–3 | League Two · Scotland |
| 2010-03-02 | Annan AthleticvForfarLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2010-02-27 | Annan AthleticvEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2010-02-20 | BerwickvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2010-02-17 | Annan AthleticvAlbion RvsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2010-02-13 | LivingstonvAnnan AthleticLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2010-02-09 | Annan AthleticvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2010-01-23 | Queens ParkvAnnan AthleticLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2009-12-12 | MontrosevAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2009-12-05 | Annan AthleticvQueens ParkLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2009-11-21 | Albion RvsvAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2009-11-14 | Annan AthleticvElginLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2009-11-07 | ForfarvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-10-31 | East StirlingvAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2009-10-17 | Annan AthleticvStranraerLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-10-13 | LivingstonvAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2009-10-10 | Annan AthleticvMontroseLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2009-09-26 | Annan AthleticvAlbion RvsLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2009-09-19 | Queens ParkvAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2009-09-12 | Annan AthleticvForfarLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-08-29 | ElginvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-08-22 | StranraervAnnan AthleticLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2009-08-15 | Annan AthleticvEast StirlingLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2009-08-08 | BerwickvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-05-09 | Annan AthleticvDumbartonLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2009-05-02 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-04-25 | Annan AthleticvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-04-18 | ForfarvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-04-11 | East StirlingvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-04-04 | Annan AthleticvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-03-28 | ElginvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2009-03-25 | Annan AthleticvAlbion RvsLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-03-21 | DumbartonvAnnan AthleticLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2009-03-14 | Annan AthleticvCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2009-03-07 | Annan AthleticvElginLeague Two · Scotland | 6–0 | League Two · Scotland |