| 2008-12-27 | East FifevBrechinLeague One · Scotland | 2–1 | League One · Scotland |
| 2008-12-20 | StranraervEast FifeLeague One · Scotland | 0–4 | League One · Scotland |
| 2008-12-13 | East FifevStirlingLeague One · Scotland | 0–1 | League One · Scotland |
| 2008-12-06 | East FifevAlloaLeague One · Scotland | 1–0 | League One · Scotland |
| 2008-11-22 | AyrvEast FifeLeague One · Scotland | 4–2 | League One · Scotland |
| 2008-11-15 | BrechinvEast FifeLeague One · Scotland | 2–1 | League One · Scotland |
| 2008-11-08 | East FifevRaith RvsLeague One · Scotland | 0–2 | League One · Scotland |
| 2008-11-01 | Queens ParkvEast FifeLeague One · Scotland | 0–0 | League One · Scotland |
| 2008-10-25 | East FifevArbroathLeague One · Scotland | 3–2 | League One · Scotland |
| 2008-10-18 | PeterheadvEast FifeLeague One · Scotland | 0–1 | League One · Scotland |
| 2008-10-04 | East FifevStranraerLeague One · Scotland | 1–2 | League One · Scotland |
| 2008-09-27 | East FifevAyrLeague One · Scotland | 3–0 | League One · Scotland |
| 2008-09-20 | AlloavEast FifeLeague One · Scotland | 0–3 | League One · Scotland |
| 2008-09-13 | Raith RvsvEast FifeLeague One · Scotland | 1–1 | League One · Scotland |
| 2008-08-30 | East FifevBrechinLeague One · Scotland | 0–0 | League One · Scotland |
| 2008-08-23 | ArbroathvEast FifeLeague One · Scotland | 0–1 | League One · Scotland |
| 2008-08-16 | East FifevQueens ParkLeague One · Scotland | 1–2 | League One · Scotland |
| 2008-08-09 | StirlingvEast FifeLeague One · Scotland | 1–1 | League One · Scotland |
| 2008-08-02 | East FifevPeterheadLeague One · Scotland | 0–2 | League One · Scotland |
| 2008-04-26 | Albion RvsvEast FifeLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2008-04-19 | East FifevArbroathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-04-12 | StenhousemuirvEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-04-05 | East FifevDumbartonLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-03-29 | ForfarvEast FifeLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2008-03-22 | East FifevMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2008-03-15 | East StirlingvEast FifeLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2008-03-08 | East FifevAlbion RvsLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2008-03-01 | StranraervEast FifeLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2008-02-23 | East FifevElginLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2008-02-16 | DumbartonvEast FifeLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2008-02-09 | East FifevStenhousemuirLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-02-02 | East FifevEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2008-01-26 | ArbroathvEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-01-19 | East FifevForfarLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2008-01-12 | MontrosevEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-01-05 | ElginvEast FifeLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-01-02 | East FifevStranraerLeague Two · Scotland | 2–1 | League Two · Scotland |