| 1999-12-27 | DundeevSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-12-18 | KilmarnockvSt JohnstonePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-11-27 | Dundee UnitedvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-11-24 | HibernianvSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-11-21 | St JohnstonevAberdeenPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-11-06 | St JohnstonevDundeePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-30 | MotherwellvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-10-27 | St JohnstonevDundee UnitedPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-10-24 | St JohnstonevCelticPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-10-16 | HeartsvSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-09-25 | RangersvSt JohnstonePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-09-19 | DundeevSt JohnstonePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-09-11 | St JohnstonevMotherwellPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-08-29 | AberdeenvSt JohnstonePremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-08-21 | St JohnstonevHibernianPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-08-15 | St JohnstonevKilmarnockPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-08-07 | CelticvSt JohnstonePremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-07-31 | St JohnstonevHeartsPremiership · Scotland | 1–4 | Premiership · Scotland |
| 1999-05-23 | St JohnstonevDundeePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-05-15 | KilmarnockvSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-05-08 | St JohnstonevMotherwellPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-01 | AberdeenvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-24 | St JohnstonevCelticPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-20 | Dundee UnitedvSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-04-17 | St JohnstonevHeartsPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-04-04 | St JohnstonevRangersPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-03-20 | DunfermlinevSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-03-13 | St JohnstonevKilmarnockPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-02-27 | DundeevSt JohnstonePremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-02-20 | HeartsvSt JohnstonePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-02-06 | St JohnstonevDundee UnitedPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-01-31 | CelticvSt JohnstonePremiership · Scotland | 5–0 | Premiership · Scotland |
| 1999-01-02 | St JohnstonevAberdeenPremiership · Scotland | 4–1 | Premiership · Scotland |