| 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 |
| 1999-10-16 | KilmarnockvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-10-02 | AberdeenvHibernianPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-02 | DundeevRangersPremiership · Scotland | 2–3 | Premiership · Scotland |
| 1999-09-25 | RangersvSt JohnstonePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-09-25 | Dundee UnitedvHeartsPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-25 | HibernianvCelticPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-25 | KilmarnockvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-19 | HibernianvKilmarnockPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-09-19 | DundeevSt JohnstonePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-09-18 | AberdeenvDundee UnitedPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-09-12 | KilmarnockvCelticPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-09-11 | Dundee UnitedvHibernianPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-09-11 | St JohnstonevMotherwellPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-09-11 | RangersvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-09-11 | HeartsvDundeePremiership · Scotland | 4–0 | Premiership · Scotland |
| 1999-08-29 | Dundee UnitedvKilmarnockPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-08-29 | AberdeenvSt JohnstonePremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-08-29 | CelticvHeartsPremiership · Scotland | 4–0 | Premiership · Scotland |
| 1999-08-28 | MotherwellvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-08-28 | HibernianvRangersPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-22 | HeartsvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-08-21 | DundeevCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-08-21 | KilmarnockvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-21 | St JohnstonevHibernianPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-08-21 | RangersvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-15 | St JohnstonevKilmarnockPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-08-15 | Dundee UnitedvCelticPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-08-15 | RangersvMotherwellPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-14 | HibernianvHeartsPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-08-14 | AberdeenvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-08-08 | DundeevHibernianPremiership · Scotland | 3–4 | Premiership · Scotland |