| 1999-11-20 | FalkirkvDunfermlineChampionship · Scotland | 1–3 | Championship · Scotland |
| 1999-11-20 | St MirrenvClydebankChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-11-14 | AyrvRaith RvsChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-11-14 | ClydebankvFalkirkChampionship · Scotland | 0–3 | Championship · Scotland |
| 1999-11-14 | DunfermlinevLivingstonChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-11-12 | AirdrievSt MirrenChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-11-12 | MortonvInverness CChampionship · Scotland | 5–1 | Championship · Scotland |
| 1999-11-06 | FalkirkvAirdrieChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-11-06 | MortonvSt MirrenChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-11-06 | AyrvClydebankChampionship · Scotland | 0–0 | Championship · Scotland |
| 1999-11-06 | DunfermlinevRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-11-06 | Inverness CvLivingstonChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-10-30 | LivingstonvFalkirkChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-30 | Raith RvsvMortonChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-30 | ClydebankvInverness CChampionship · Scotland | 0–3 | Championship · Scotland |
| 1999-10-30 | St MirrenvDunfermlineChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-30 | AirdrievAyrChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-10-23 | AyrvSt MirrenChampionship · Scotland | 0–3 | Championship · Scotland |
| 1999-10-23 | MortonvFalkirkChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-10-23 | Raith RvsvLivingstonChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-23 | Inverness CvDunfermlineChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-23 | AirdrievClydebankChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-10-16 | ClydebankvMortonChampionship · Scotland | 1–3 | Championship · Scotland |
| 1999-10-16 | LivingstonvAyrChampionship · Scotland | 4–1 | Championship · Scotland |
| 1999-10-16 | St MirrenvRaith RvsChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-10-16 | DunfermlinevAirdrieChampionship · Scotland | 0–0 | Championship · Scotland |
| 1999-10-16 | FalkirkvInverness CChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-10-09 | ClydebankvDunfermlineChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-10-02 | AirdrievInverness CChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-02 | AyrvMortonChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-10-02 | Raith RvsvFalkirkChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-10-02 | St MirrenvLivingstonChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-09-25 | LivingstonvClydebankChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-09-25 | DunfermlinevAyrChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-09-25 | Inverness CvRaith RvsChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-25 | FalkirkvSt MirrenChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-09-25 | MortonvAirdrieChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-18 | ClydebankvAyrChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-18 | LivingstonvInverness CChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-09-18 | St MirrenvMortonChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-09-18 | Raith RvsvDunfermlineChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-09-18 | AirdrievFalkirkChampionship · Scotland | 0–0 | Championship · Scotland |
| 1999-09-11 | FalkirkvLivingstonChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-11 | MortonvRaith RvsChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-09-11 | AyrvAirdrieChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-09-11 | Inverness CvClydebankChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-09-11 | DunfermlinevSt MirrenChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-09-04 | FalkirkvClydebankChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-09-04 | Raith RvsvAyrChampionship · Scotland | 5–1 | Championship · Scotland |
| 1999-09-04 | Inverness CvMortonChampionship · Scotland | 1–1 | Championship · Scotland |