| 1999-11-28 | RangersvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-11-20 | RangersvHibernianPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-11-07 | RangersvCelticPremiership · Scotland | 4–2 | Premiership · Scotland |
| 1999-10-30 | AberdeenvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-10-16 | KilmarnockvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-10-02 | DundeevRangersPremiership · Scotland | 2–3 | Premiership · Scotland |
| 1999-09-25 | RangersvSt JohnstonePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-09-11 | RangersvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-08-28 | HibernianvRangersPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-21 | RangersvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-15 | RangersvMotherwellPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-07 | HeartsvRangersPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-07-31 | RangersvKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-05-23 | RangersvKilmarnockPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-05-15 | MotherwellvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-05-09 | RangersvHeartsPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-02 | CelticvRangersPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-04-25 | RangersvAberdeenPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-04-18 | DundeevRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-04-14 | RangersvDunfermlinePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-04 | St JohnstonevRangersPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-03-20 | RangersvDundee UnitedPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-03-13 | RangersvMotherwellPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-02-27 | KilmarnockvRangersPremiership · Scotland | 0–5 | Premiership · Scotland |
| 1999-02-20 | RangersvDundeePremiership · Scotland | 6–1 | Premiership · Scotland |
| 1999-02-07 | DunfermlinevRangersPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-01-30 | AberdeenvRangersPremiership · Scotland | 2–4 | Premiership · Scotland |
| 1999-01-27 | DundeevRangersPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-01-03 | RangersvCelticPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1998-12-30 | Dundee UnitedvRangersPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1998-12-26 | RangersvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-12-19 | HeartsvRangersPremiership · Scotland | 2–3 | Premiership · Scotland |
| 1998-12-12 | RangersvKilmarnockPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-12-05 | RangersvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1998-11-21 | CelticvRangersPremiership · Scotland | 5–1 | Premiership · Scotland |
| 1998-11-14 | RangersvAberdeenPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1998-11-08 | St JohnstonevRangersPremiership · Scotland | 0–7 | Premiership · Scotland |
| 1998-10-30 | RangersvDundee UnitedPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1998-10-28 | MotherwellvRangersPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-10-17 | RangersvHeartsPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1998-10-04 | RangersvDundeePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-09-26 | DunfermlinevRangersPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1998-09-23 | AberdeenvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1998-09-20 | RangersvCelticPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1998-09-12 | Dundee UnitedvRangersPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1998-08-29 | RangersvSt JohnstonePremiership · Scotland | 4–0 | Premiership · Scotland |
| 1998-08-22 | KilmarnockvRangersPremiership · Scotland | 1–3 | Premiership · Scotland |
| 1998-08-15 | RangersvMotherwellPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1998-08-02 | HeartsvRangersPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1998-05-09 | Dundee UnitedvRangersPremiership · Scotland | 1–2 | Premiership · Scotland |