| 1999-12-18 | DunfermlinevInverness CChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-12-11 | MortonvDunfermlineChampionship · Scotland | 0–3 | Championship · Scotland |
| 1999-12-04 | AyrvDunfermlineChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-11-27 | DunfermlinevClydebankChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-11-20 | FalkirkvDunfermlineChampionship · Scotland | 1–3 | Championship · Scotland |
| 1999-11-14 | DunfermlinevLivingstonChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-11-06 | DunfermlinevRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-30 | St MirrenvDunfermlineChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-23 | Inverness CvDunfermlineChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-16 | DunfermlinevAirdrieChampionship · Scotland | 0–0 | Championship · Scotland |
| 1999-10-09 | ClydebankvDunfermlineChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-09-25 | DunfermlinevAyrChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-09-18 | Raith RvsvDunfermlineChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-09-11 | DunfermlinevSt MirrenChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-09-04 | LivingstonvDunfermlineChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-08-28 | DunfermlinevFalkirkChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-08-21 | DunfermlinevMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-08-14 | AirdrievDunfermlineChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-08-07 | DunfermlinevInverness CChampionship · Scotland | 4–0 | Championship · Scotland |
| 1999-05-23 | DunfermlinevMotherwellPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-15 | DundeevDunfermlinePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-05-08 | DunfermlinevCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-03 | HeartsvDunfermlinePremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-04-24 | DunfermlinevDundee UnitedPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-04-17 | DunfermlinevKilmarnockPremiership · Scotland | 0–6 | Premiership · Scotland |
| 1999-04-14 | RangersvDunfermlinePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-03 | AberdeenvDunfermlinePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-03-20 | DunfermlinevSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-03-13 | DunfermlinevDundeePremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-03-06 | KilmarnockvDunfermlinePremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-02-27 | MotherwellvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-02-07 | DunfermlinevRangersPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-01-30 | Dundee UnitedvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-01-02 | DunfermlinevHeartsPremiership · Scotland | 0–0 | Premiership · Scotland |