| 1999-12-18 | MotherwellvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-12-11 | HibernianvMotherwellPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-11-28 | MotherwellvCelticPremiership · Scotland | 3–2 | Premiership · Scotland |
| 1999-11-23 | MotherwellvHeartsPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-11-20 | DundeevMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-11-06 | HeartsvMotherwellPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-10-30 | MotherwellvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-10-27 | CelticvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-23 | Dundee UnitedvMotherwellPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-10-20 | MotherwellvAberdeenPremiership · Scotland | 5–6 | Premiership · Scotland |
| 1999-10-16 | MotherwellvHibernianPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-09-11 | St JohnstonevMotherwellPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-08-28 | MotherwellvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-08-21 | KilmarnockvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-15 | RangersvMotherwellPremiership · Scotland | 4–1 | Premiership · Scotland |
| 1999-08-07 | MotherwellvDundee UnitedPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-07-31 | HibernianvMotherwellPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-05-23 | DunfermlinevMotherwellPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-15 | MotherwellvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-05-08 | St JohnstonevMotherwellPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-01 | KilmarnockvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-04-24 | MotherwellvHeartsPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-04-17 | CelticvMotherwellPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-10 | MotherwellvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-04-03 | Dundee UnitedvMotherwellPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-03-20 | MotherwellvAberdeenPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-03-13 | RangersvMotherwellPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-02-27 | MotherwellvDunfermlinePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-02-21 | MotherwellvCelticPremiership · Scotland | 1–7 | Premiership · Scotland |
| 1999-02-06 | DundeevMotherwellPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-01-30 | HeartsvMotherwellPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-01-01 | MotherwellvKilmarnockPremiership · Scotland | 1–2 | Premiership · Scotland |