| 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 |
| 1998-12-30 | Dundee UnitedvRangersPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1998-12-26 | MotherwellvDundee UnitedPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1998-12-20 | KilmarnockvDundee UnitedPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1998-12-12 | Dundee UnitedvCelticPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1998-12-05 | Dundee UnitedvSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1998-11-28 | AberdeenvDundee UnitedPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1998-11-22 | Dundee UnitedvDundeePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1998-11-15 | DunfermlinevDundee UnitedPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1998-11-07 | Dundee UnitedvMotherwellPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1998-10-30 | RangersvDundee UnitedPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1998-10-24 | HeartsvDundee UnitedPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1998-10-17 | Dundee UnitedvKilmarnockPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1998-10-04 | Dundee UnitedvAberdeenPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-09-26 | St JohnstonevDundee UnitedPremiership · Scotland | 1–3 | Premiership · Scotland |
| 1998-09-23 | Dundee UnitedvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1998-09-19 | DundeevDundee UnitedPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1998-09-12 | Dundee UnitedvRangersPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1998-08-30 | MotherwellvDundee UnitedPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-08-22 | CelticvDundee UnitedPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1998-08-16 | Dundee UnitedvHeartsPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1998-08-01 | KilmarnockvDundee UnitedPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1998-05-09 | Dundee UnitedvRangersPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1998-05-02 | HibernianvDundee UnitedPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1998-04-25 | Dundee UnitedvSt JohnstonePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1998-04-18 | KilmarnockvDundee UnitedPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-04-11 | Dundee UnitedvAberdeenPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1998-04-07 | Dundee UnitedvDunfermlinePremiership · Scotland | 2–2 | Premiership · Scotland |
| 1998-03-28 | MotherwellvDundee UnitedPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1998-03-21 | Dundee UnitedvHeartsPremiership · Scotland | 0–1 | Premiership · Scotland |