| 1999-12-27 | AberdeenvDundee UnitedPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-12-18 | CelticvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-12-12 | Dundee UnitedvDundeePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-12-05 | HeartsvDundee UnitedPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-11-27 | Dundee UnitedvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-11-20 | KilmarnockvDundee UnitedPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-11-06 | Dundee UnitedvAberdeenPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-10-31 | HibernianvDundee UnitedPremiership · Scotland | 3–2 | Premiership · Scotland |
| 1999-10-27 | St JohnstonevDundee UnitedPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-23 | Dundee UnitedvMotherwellPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-10-17 | DundeevDundee UnitedPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-25 | Dundee UnitedvHeartsPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-18 | AberdeenvDundee UnitedPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-09-11 | Dundee UnitedvHibernianPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-08-29 | Dundee UnitedvKilmarnockPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-08-21 | RangersvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-15 | Dundee UnitedvCelticPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-08-07 | MotherwellvDundee UnitedPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-07-31 | Dundee UnitedvDundeePremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-05-23 | Dundee UnitedvCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-15 | HeartsvDundee UnitedPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-05-08 | Dundee UnitedvKilmarnockPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-01 | Dundee UnitedvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-04-24 | DunfermlinevDundee UnitedPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-04-20 | Dundee UnitedvSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-04-17 | AberdeenvDundee UnitedPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-04-06 | Dundee UnitedvHeartsPremiership · Scotland | 1–3 | Premiership · Scotland |
| 1999-04-03 | Dundee UnitedvMotherwellPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-03-20 | RangersvDundee UnitedPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-02-27 | CelticvDundee UnitedPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-02-20 | Dundee UnitedvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-02-06 | St JohnstonevDundee UnitedPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-01-30 | Dundee UnitedvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-01-02 | DundeevDundee UnitedPremiership · Scotland | 1–3 | Premiership · Scotland |