| 1999-12-27 | DundeevSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-12-12 | Dundee UnitedvDundeePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-11-28 | RangersvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-11-20 | DundeevMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-11-06 | St JohnstonevDundeePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-30 | DundeevHeartsPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-10-23 | HibernianvDundeePremiership · Scotland | 5–2 | Premiership · Scotland |
| 1999-10-17 | DundeevDundee UnitedPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-10-02 | DundeevRangersPremiership · Scotland | 2–3 | Premiership · Scotland |
| 1999-09-25 | KilmarnockvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-19 | DundeevSt JohnstonePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-09-11 | HeartsvDundeePremiership · Scotland | 4–0 | Premiership · Scotland |
| 1999-08-28 | MotherwellvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-08-21 | DundeevCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-08-14 | AberdeenvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-08-08 | DundeevHibernianPremiership · Scotland | 3–4 | Premiership · Scotland |
| 1999-07-31 | Dundee UnitedvDundeePremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-05-23 | St JohnstonevDundeePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-05-15 | DundeevDunfermlinePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-05-08 | AberdeenvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-01 | Dundee UnitedvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-04-24 | DundeevKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-04-18 | DundeevRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-04-10 | MotherwellvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-04-03 | CelticvDundeePremiership · Scotland | 5–0 | Premiership · Scotland |
| 1999-03-20 | DundeevHeartsPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-03-13 | DunfermlinevDundeePremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-02-27 | DundeevSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-02-20 | RangersvDundeePremiership · Scotland | 6–1 | Premiership · Scotland |
| 1999-02-06 | DundeevMotherwellPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-01-30 | KilmarnockvDundeePremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-01-27 | DundeevRangersPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-01-02 | DundeevDundee UnitedPremiership · Scotland | 1–3 | Premiership · Scotland |