| 1999-12-27 | MortonvRaith RvsChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-12-04 | Raith RvsvInverness CChampionship · Scotland | 4–2 | Championship · Scotland |
| 1999-11-27 | FalkirkvRaith RvsChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-11-20 | Raith RvsvAirdrieChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-11-14 | AyrvRaith RvsChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-11-06 | DunfermlinevRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-30 | Raith RvsvMortonChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-23 | Raith RvsvLivingstonChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-16 | St MirrenvRaith RvsChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-10-02 | Raith RvsvFalkirkChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-09-25 | Inverness CvRaith RvsChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-18 | Raith RvsvDunfermlineChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-09-11 | MortonvRaith RvsChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-09-04 | Raith RvsvAyrChampionship · Scotland | 5–1 | Championship · Scotland |
| 1999-08-28 | AirdrievRaith RvsChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-08-21 | ClydebankvRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-08-14 | Raith RvsvSt MirrenChampionship · Scotland | 0–6 | Championship · Scotland |
| 1999-08-07 | LivingstonvRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-05-08 | AyrvRaith RvsChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-05-01 | Raith RvsvSt MirrenChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-04-24 | HamiltonvRaith RvsChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-04-17 | FalkirkvRaith RvsChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-04-10 | Raith RvsvHibernianChampionship · Scotland | 1–3 | Championship · Scotland |
| 1999-04-03 | Raith RvsvStranraerChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-03-20 | ClydebankvRaith RvsChampionship · Scotland | 0–0 | Championship · Scotland |
| 1999-03-13 | MortonvRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-02-27 | Raith RvsvAirdrieChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-02-20 | Raith RvsvAyrChampionship · Scotland | 2–4 | Championship · Scotland |
| 1999-02-06 | St MirrenvRaith RvsChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-01-30 | Raith RvsvClydebankChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-01-16 | StranraervRaith RvsChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-01-09 | Raith RvsvFalkirkChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-01-02 | HibernianvRaith RvsChampionship · Scotland | 5–1 | Championship · Scotland |