| 1999-12-27 | CelticvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-12-22 | RangersvHeartsPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-12-18 | MotherwellvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-12-11 | RangersvKilmarnockPremiership · Scotland | 1–0 | Premiership · Scotland |
| 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 |
| 1999-11-03 | Bayern MunichvRangersUEFA Champions League | 1–0 | UEFA Champions League |
| 1999-10-30 | AberdeenvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-10-26 | RangersvValenciaUEFA Champions League | 1–2 | UEFA Champions League |
| 1999-10-20 | RangersvPSV EindhovenUEFA Champions League | 4–1 | UEFA Champions League |
| 1999-10-16 | KilmarnockvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-10-02 | DundeevRangersPremiership · Scotland | 2–3 | Premiership · Scotland |
| 1999-09-28 | PSV EindhovenvRangersUEFA Champions League | 0–1 | UEFA Champions League |
| 1999-09-25 | RangersvSt JohnstonePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-09-21 | RangersvBayern MunichUEFA Champions League | 1–1 | UEFA Champions League |
| 1999-09-15 | ValenciavRangersUEFA Champions League | 2–0 | UEFA Champions League |
| 1999-09-11 | RangersvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-08-28 | HibernianvRangersPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-25 | ParmavRangersUEFA Champions League | 1–0 | UEFA Champions League |
| 1999-08-21 | RangersvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-15 | RangersvMotherwellPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-11 | RangersvParmaUEFA Champions League | 2–0 | UEFA Champions League |
| 1999-08-07 | HeartsvRangersPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-08-04 | RangersvHakaUEFA Champions League | 3–0 | UEFA Champions League |
| 1999-07-31 | RangersvKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-07-28 | HakavRangersUEFA Champions League | 1–4 | UEFA Champions League |
| 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 |