| 1999-08-07 | CelticvSt JohnstonePremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-08-07 | KilmarnockvAberdeenPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-08-07 | HeartsvRangersPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-08-07 | MotherwellvDundee UnitedPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-08-01 | AberdeenvCelticPremiership · Scotland | 0–5 | Premiership · Scotland |
| 1999-07-31 | Dundee UnitedvDundeePremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-07-31 | HibernianvMotherwellPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-07-31 | St JohnstonevHeartsPremiership · Scotland | 1–4 | Premiership · Scotland |
| 1999-07-31 | RangersvKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-05-23 | RangersvKilmarnockPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-05-23 | AberdeenvHeartsPremiership · Scotland | 2–5 | Premiership · Scotland |
| 1999-05-23 | St JohnstonevDundeePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-05-23 | Dundee UnitedvCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-23 | DunfermlinevMotherwellPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-15 | KilmarnockvSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-05-15 | MotherwellvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-05-15 | CelticvAberdeenPremiership · Scotland | 3–2 | Premiership · Scotland |
| 1999-05-15 | HeartsvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-05-15 | DundeevDunfermlinePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-05-09 | RangersvHeartsPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-08 | Dundee UnitedvKilmarnockPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-08 | AberdeenvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-08 | DunfermlinevCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-08 | St JohnstonevMotherwellPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-03 | HeartsvDunfermlinePremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-05-02 | CelticvRangersPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-05-01 | KilmarnockvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-05-01 | Dundee UnitedvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-05-01 | AberdeenvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-25 | RangersvAberdeenPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-04-24 | DundeevKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-04-24 | St JohnstonevCelticPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-24 | DunfermlinevDundee UnitedPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-04-24 | MotherwellvHeartsPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-04-20 | Dundee UnitedvSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-04-18 | DundeevRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-04-17 | St JohnstonevHeartsPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-04-17 | AberdeenvDundee UnitedPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-04-17 | CelticvMotherwellPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-17 | DunfermlinevKilmarnockPremiership · Scotland | 0–6 | Premiership · Scotland |
| 1999-04-14 | HeartsvCelticPremiership · Scotland | 2–4 | Premiership · Scotland |
| 1999-04-14 | RangersvDunfermlinePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-10 | MotherwellvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-04-10 | KilmarnockvAberdeenPremiership · Scotland | 4–2 | Premiership · Scotland |
| 1999-04-06 | Dundee UnitedvHeartsPremiership · Scotland | 1–3 | Premiership · Scotland |
| 1999-04-04 | St JohnstonevRangersPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-04-03 | Dundee UnitedvMotherwellPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-04-03 | AberdeenvDunfermlinePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-04-03 | CelticvDundeePremiership · Scotland | 5–0 | Premiership · Scotland |
| 1999-04-03 | HeartsvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |