| 1999-12-27 | BerwickvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-12-18 | MontrosevCowdenbeathLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-12-07 | ForfarvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-11-27 | MontrosevQueens ParkLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-11-20 | MontrosevEast FifeLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-11-14 | East StirlingvMontroseLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-11-06 | BrechinvMontroseLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-10-30 | MontrosevAlbion RvsLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-10-23 | CowdenbeathvMontroseLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-10-16 | MontrosevDumbartonLeague Two · Scotland | 1–4 | League Two · Scotland |
| 1999-10-02 | Queens ParkvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-09-28 | MontrosevForfarLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-09-18 | MontrosevBrechinLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-09-11 | Albion RvsvMontroseLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-09-04 | MontrosevEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-08-28 | East FifevMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-08-21 | MontrosevBerwickLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-08-14 | DumbartonvMontroseLeague Two · Scotland | 3–4 | League Two · Scotland |
| 1999-08-07 | MontrosevCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-05-08 | MontrosevCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-05-01 | BerwickvMontroseLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-04-24 | MontrosevRoss CountyLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-04-17 | MontrosevStenhousemuirLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-10 | Queens ParkvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-03 | DumbartonvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-20 | MontrosevEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-03-16 | Albion RvsvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-03-13 | MontrosevBrechinLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-02-27 | MontrosevBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-02-23 | StenhousemuirvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1999-02-20 | CowdenbeathvMontroseLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-02-16 | BrechinvMontroseLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-02-06 | MontrosevQueens ParkLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1999-01-30 | East StirlingvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-01-16 | MontrosevDumbartonLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1999-01-09 | MontrosevAlbion RvsLeague Two · Scotland | 2–3 | League Two · Scotland |