| 2008-12-27 | StenhousemuirvAnnan AthleticLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2008-12-20 | Annan AthleticvDumbartonLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-12-13 | Annan AthleticvBerwickLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-11-22 | Annan AthleticvElginLeague Two · Scotland | 5–0 | League Two · Scotland |
| 2008-11-15 | Albion RvsvAnnan AthleticLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-11-12 | East StirlingvAnnan AthleticLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-11-08 | Annan AthleticvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-10-18 | Annan AthleticvCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-10-04 | DumbartonvAnnan AthleticLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2008-09-27 | BerwickvAnnan AthleticLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2008-09-20 | Annan AthleticvForfarLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2008-09-13 | ElginvAnnan AthleticLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-08-30 | Annan AthleticvAlbion RvsLeague Two · Scotland | 2–4 | League Two · Scotland |
| 2008-08-23 | MontrosevAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2008-08-16 | Annan AthleticvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-08-09 | Annan AthleticvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2008-08-02 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–4 | League Two · Scotland |