| 1998-12-19 | Ross CountyvMontroseLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1998-12-12 | MontrosevCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-11-28 | MontrosevEast StirlingLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1998-11-25 | DumbartonvMontroseLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-11-14 | MontrosevStenhousemuirLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1998-11-07 | Queens ParkvMontroseLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1998-10-31 | Albion RvsvMontroseLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1998-10-27 | MontrosevBrechinLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-10-17 | MontrosevRoss CountyLeague Two · Scotland | 3–6 | League Two · Scotland |
| 1998-10-11 | BerwickvMontroseLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-10-03 | East StirlingvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-09-26 | MontrosevDumbartonLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-09-19 | MontrosevQueens ParkLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-09-12 | StenhousemuirvMontroseLeague Two · Scotland | 4–0 | League Two · Scotland |
| 1998-09-05 | MontrosevAlbion RvsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-08-29 | BrechinvMontroseLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1998-08-22 | Ross CountyvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-08-15 | MontrosevBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-08-04 | CowdenbeathvMontroseLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1998-05-09 | Albion RvsvMontroseLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1998-05-02 | MontrosevDumbartonLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1998-04-25 | ArbroathvMontroseLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1998-04-18 | MontrosevAlloaLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1998-04-11 | CowdenbeathvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1998-04-04 | MontrosevQueens ParkLeague Two · Scotland | 4–3 | League Two · Scotland |
| 1998-03-28 | BerwickvMontroseLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-03-21 | MontrosevEast StirlingLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-03-14 | Ross CountyvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1998-03-10 | MontrosevRoss CountyLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-03-07 | AlloavMontroseLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1998-02-28 | MontrosevCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-02-25 | DumbartonvMontroseLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1998-02-21 | MontrosevAlbion RvsLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1998-02-14 | Queens ParkvMontroseLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-02-07 | MontrosevBerwickLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1998-01-31 | East StirlingvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-01-10 | Albion RvsvMontroseLeague Two · Scotland | 3–2 | League Two · Scotland |