| 1999-12-27 | HibernianvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-12-18 | KilmarnockvSt JohnstonePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-12-11 | RangersvKilmarnockPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-11-27 | KilmarnockvHeartsPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-11-20 | KilmarnockvDundee UnitedPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-11-06 | KilmarnockvHibernianPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-10-30 | CelticvKilmarnockPremiership · Scotland | 5–1 | Premiership · Scotland |
| 1999-10-27 | HeartsvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-23 | AberdeenvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-16 | KilmarnockvRangersPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-09-25 | KilmarnockvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-19 | HibernianvKilmarnockPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-09-12 | KilmarnockvCelticPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-29 | Dundee UnitedvKilmarnockPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-08-21 | KilmarnockvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-15 | St JohnstonevKilmarnockPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-08-07 | KilmarnockvAberdeenPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-07-31 | RangersvKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-05-23 | RangersvKilmarnockPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-05-15 | KilmarnockvSt JohnstonePremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-05-08 | Dundee UnitedvKilmarnockPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-05-01 | KilmarnockvMotherwellPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-04-24 | DundeevKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-04-17 | DunfermlinevKilmarnockPremiership · Scotland | 0–6 | Premiership · Scotland |
| 1999-04-10 | KilmarnockvAberdeenPremiership · Scotland | 4–2 | Premiership · Scotland |
| 1999-04-03 | HeartsvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-03-21 | KilmarnockvCelticPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-03-13 | St JohnstonevKilmarnockPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-03-06 | KilmarnockvDunfermlinePremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-02-27 | KilmarnockvRangersPremiership · Scotland | 0–5 | Premiership · Scotland |
| 1999-02-17 | CelticvKilmarnockPremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-02-06 | AberdeenvKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-01-30 | KilmarnockvDundeePremiership · Scotland | 0–0 | Premiership · Scotland |
| 1999-01-01 | MotherwellvKilmarnockPremiership · Scotland | 1–2 | Premiership · Scotland |