| 1999-12-27 | DundeevSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-12-27 | AberdeenvDundee UnitedPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-12-27 | CelticvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-12-27 | HibernianvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-12-22 | RangersvHeartsPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-12-19 | HeartsvHibernianPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-12-18 | CelticvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-12-18 | KilmarnockvSt JohnstonePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-12-18 | MotherwellvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-12-12 | Dundee UnitedvDundeePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-12-11 | RangersvKilmarnockPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-12-11 | AberdeenvCelticPremiership · Scotland | 0–6 | Premiership · Scotland |
| 1999-12-11 | HibernianvMotherwellPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-12-08 | AberdeenvHeartsPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-12-05 | HeartsvDundee UnitedPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-12-04 | CelticvHibernianPremiership · Scotland | 4–0 | Premiership · Scotland |
| 1999-11-28 | RangersvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-11-28 | MotherwellvCelticPremiership · Scotland | 3–2 | Premiership · Scotland |
| 1999-11-27 | Dundee UnitedvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-11-27 | HibernianvAberdeenPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-11-27 | KilmarnockvHeartsPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-11-24 | HibernianvSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-11-23 | MotherwellvHeartsPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-11-21 | St JohnstonevAberdeenPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-11-20 | DundeevMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-11-20 | HeartsvCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-11-20 | RangersvHibernianPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-11-20 | KilmarnockvDundee UnitedPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-11-07 | RangersvCelticPremiership · Scotland | 4–2 | Premiership · Scotland |
| 1999-11-06 | KilmarnockvHibernianPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-11-06 | HeartsvMotherwellPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-11-06 | Dundee UnitedvAberdeenPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-11-06 | St JohnstonevDundeePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-31 | HibernianvDundee UnitedPremiership · Scotland | 3–2 | Premiership · Scotland |
| 1999-10-30 | MotherwellvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-10-30 | CelticvKilmarnockPremiership · Scotland | 5–1 | Premiership · Scotland |
| 1999-10-30 | AberdeenvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-10-30 | DundeevHeartsPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-10-27 | St JohnstonevDundee UnitedPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-27 | HeartsvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-27 | CelticvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-24 | St JohnstonevCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-10-23 | Dundee UnitedvMotherwellPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-10-23 | AberdeenvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-23 | HibernianvDundeePremiership · Scotland | 5–2 | Premiership · Scotland |
| 1999-10-20 | MotherwellvAberdeenPremiership · Scotland | 5–6 | Premiership · Scotland |
| 1999-10-17 | DundeevDundee UnitedPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-10-16 | MotherwellvHibernianPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-16 | CelticvAberdeenPremiership · Scotland | 7–0 | Premiership · Scotland |
| 1999-10-16 | HeartsvSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |