| 2008-12-27 | BerwickvMontroseLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2008-12-20 | MontrosevAlbion RvsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-12-13 | MontrosevCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-12-06 | East StirlingvMontroseLeague Two · Scotland | 5–0 | League Two · Scotland |
| 2008-11-22 | MontrosevForfarLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2008-11-15 | ElginvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-11-08 | Annan AthleticvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-11-01 | MontrosevStenhousemuirLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2008-10-18 | MontrosevDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-10-04 | Albion RvsvMontroseLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-09-27 | CowdenbeathvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-09-20 | MontrosevEast StirlingLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2008-09-13 | ForfarvMontroseLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-08-30 | MontrosevElginLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2008-08-23 | MontrosevAnnan AthleticLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2008-08-16 | StenhousemuirvMontroseLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2008-08-09 | MontrosevBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2008-08-02 | DumbartonvMontroseLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2008-04-26 | East StirlingvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2008-04-19 | MontrosevElginLeague Two · Scotland | 3–2 | League Two · Scotland |
| 2008-04-12 | DumbartonvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2008-04-05 | MontrosevForfarLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2008-03-29 | MontrosevStenhousemuirLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-03-22 | East FifevMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2008-03-15 | Albion RvsvMontroseLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2008-03-08 | MontrosevEast StirlingLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2008-03-01 | ArbroathvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-02-23 | MontrosevStranraerLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2008-02-16 | ForfarvMontroseLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2008-02-09 | MontrosevDumbartonLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2008-02-02 | MontrosevAlbion RvsLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-01-26 | ElginvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-01-19 | StenhousemuirvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2008-01-12 | MontrosevEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-01-05 | StranraervMontroseLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2008-01-02 | MontrosevArbroathLeague Two · Scotland | 5–0 | League Two · Scotland |