| 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 |
| 2009-03-03 | ForfarvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-02-28 | Albion RvsvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-02-24 | BerwickvAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-02-21 | Annan AthleticvForfarLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-02-07 | Annan AthleticvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-01-31 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-01-24 | Annan AthleticvEast StirlingLeague Two · Scotland | 4–0 | League Two · Scotland |
| 2009-01-17 | MontrosevAnnan AthleticLeague Two · Scotland | 0–3 | League Two · Scotland |