| 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 |