| 2023-12-30 | MontrosevCove RangersLeague One · Scotland | 1–1 | League One · Scotland |
| 2023-12-23 | AlloavMontroseLeague One · Scotland | 2–2 | League One · Scotland |
| 2023-12-16 | Kelty HeartsvMontroseLeague One · Scotland | 0–1 | League One · Scotland |
| 2023-12-09 | MontrosevQueen of SthLeague One · Scotland | 1–4 | League One · Scotland |
| 2023-11-28 | MontrosevFalkirkLeague One · Scotland | 0–0 | League One · Scotland |
| 2023-11-14 | Cove RangersvMontroseLeague One · Scotland | 1–0 | League One · Scotland |
| 2023-11-11 | MontrosevAnnan AthleticLeague One · Scotland | 1–1 | League One · Scotland |
| 2023-11-04 | Edinburgh CityvMontroseLeague One · Scotland | 1–5 | League One · Scotland |
| 2023-10-28 | MontrosevHamiltonLeague One · Scotland | 0–3 | League One · Scotland |
| 2023-10-07 | MontrosevAlloaLeague One · Scotland | 2–1 | League One · Scotland |
| 2023-09-30 | FalkirkvMontroseLeague One · Scotland | 3–2 | League One · Scotland |
| 2023-09-23 | MontrosevStirlingLeague One · Scotland | 1–0 | League One · Scotland |
| 2023-09-16 | MontrosevEdinburgh CityLeague One · Scotland | 5–2 | League One · Scotland |
| 2023-09-02 | Queen of SthvMontroseLeague One · Scotland | 2–3 | League One · Scotland |
| 2023-08-26 | HamiltonvMontroseLeague One · Scotland | 1–0 | League One · Scotland |
| 2023-08-19 | MontrosevCove RangersLeague One · Scotland | 0–3 | League One · Scotland |
| 2023-08-12 | Annan AthleticvMontroseLeague One · Scotland | 1–3 | League One · Scotland |
| 2023-08-05 | MontrosevKelty HeartsLeague One · Scotland | 0–2 | League One · Scotland |
| 2023-05-06 | ClydevMontroseLeague One · Scotland | 2–1 | League One · Scotland |
| 2023-04-29 | MontrosevAlloaLeague One · Scotland | 0–4 | League One · Scotland |
| 2023-04-22 | Queen of SthvMontroseLeague One · Scotland | 2–3 | League One · Scotland |
| 2023-04-15 | MontrosevPeterheadLeague One · Scotland | 2–1 | League One · Scotland |
| 2023-04-11 | MontrosevFalkirkLeague One · Scotland | 1–2 | League One · Scotland |
| 2023-04-08 | Airdrie UtdvMontroseLeague One · Scotland | 3–0 | League One · Scotland |
| 2023-04-01 | FC EdinburghvMontroseLeague One · Scotland | 1–1 | League One · Scotland |
| 2023-03-25 | MontrosevDunfermlineLeague One · Scotland | 1–3 | League One · Scotland |
| 2023-03-18 | Kelty HeartsvMontroseLeague One · Scotland | 1–2 | League One · Scotland |
| 2023-03-04 | MontrosevClydeLeague One · Scotland | 2–0 | League One · Scotland |
| 2023-02-25 | AlloavMontroseLeague One · Scotland | 1–0 | League One · Scotland |
| 2023-02-18 | MontrosevFC EdinburghLeague One · Scotland | 3–3 | League One · Scotland |
| 2023-02-04 | DunfermlinevMontroseLeague One · Scotland | 2–0 | League One · Scotland |
| 2023-01-28 | MontrosevKelty HeartsLeague One · Scotland | 3–3 | League One · Scotland |
| 2023-01-14 | MontrosevQueen of SthLeague One · Scotland | 1–0 | League One · Scotland |
| 2023-01-07 | FalkirkvMontroseLeague One · Scotland | 2–1 | League One · Scotland |
| 2023-01-02 | PeterheadvMontroseLeague One · Scotland | 0–0 | League One · Scotland |