| 1999-12-27 | MortonvRaith RvsChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-12-18 | FalkirkvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-12-11 | MortonvDunfermlineChampionship · Scotland | 0–3 | Championship · Scotland |
| 1999-12-07 | AirdrievMortonChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-11-27 | MortonvAyrChampionship · Scotland | 0–0 | Championship · Scotland |
| 1999-11-20 | LivingstonvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-11-12 | MortonvInverness CChampionship · Scotland | 5–1 | Championship · Scotland |
| 1999-11-06 | MortonvSt MirrenChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-10-30 | Raith RvsvMortonChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-23 | MortonvFalkirkChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-10-16 | ClydebankvMortonChampionship · Scotland | 1–3 | Championship · Scotland |
| 1999-10-02 | AyrvMortonChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-09-25 | MortonvAirdrieChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-18 | St MirrenvMortonChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-09-11 | MortonvRaith RvsChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-09-04 | Inverness CvMortonChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-08-28 | MortonvLivingstonChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-08-21 | DunfermlinevMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-08-14 | MortonvClydebankChampionship · Scotland | 0–0 | Championship · Scotland |
| 1999-08-07 | FalkirkvMortonChampionship · Scotland | 2–4 | Championship · Scotland |
| 1999-05-08 | HamiltonvMortonChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-05-01 | MortonvAyrChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-04-24 | HibernianvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-04-21 | ClydebankvMortonChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-04-17 | MortonvAirdrieChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-04-10 | St MirrenvMortonChampionship · Scotland | 1–5 | Championship · Scotland |
| 1999-04-03 | MortonvFalkirkChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-03-20 | StranraervMortonChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-03-13 | MortonvRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-02-20 | MortonvHamiltonChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-02-06 | AyrvMortonChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-01-30 | MortonvStranraerChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-01-19 | AirdrievMortonChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-01-16 | FalkirkvMortonChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-01-05 | MortonvSt MirrenChampionship · Scotland | 0–0 | Championship · Scotland |