| 1999-12-27 | AberdeenvDundee UnitedPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-12-11 | AberdeenvCelticPremiership · Scotland | 0–6 | Premiership · Scotland |
| 1999-12-08 | AberdeenvHeartsPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-11-27 | HibernianvAberdeenPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-11-21 | St JohnstonevAberdeenPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-11-06 | Dundee UnitedvAberdeenPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-10-30 | AberdeenvRangersPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-10-23 | AberdeenvKilmarnockPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-20 | MotherwellvAberdeenPremiership · Scotland | 5–6 | Premiership · Scotland |
| 1999-10-16 | CelticvAberdeenPremiership · Scotland | 7–0 | Premiership · Scotland |
| 1999-10-02 | AberdeenvHibernianPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-09-18 | AberdeenvDundee UnitedPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-09-11 | RangersvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-08-29 | AberdeenvSt JohnstonePremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-08-22 | HeartsvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-08-14 | AberdeenvDundeePremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-08-07 | KilmarnockvAberdeenPremiership · Scotland | 2–0 | Premiership · Scotland |
| 1999-08-01 | AberdeenvCelticPremiership · Scotland | 0–5 | Premiership · Scotland |
| 1999-05-23 | AberdeenvHeartsPremiership · Scotland | 2–5 | Premiership · Scotland |
| 1999-05-15 | CelticvAberdeenPremiership · Scotland | 3–2 | Premiership · Scotland |
| 1999-05-08 | AberdeenvDundeePremiership · Scotland | 1–2 | Premiership · Scotland |
| 1999-05-01 | AberdeenvSt JohnstonePremiership · Scotland | 1–0 | Premiership · Scotland |
| 1999-04-25 | RangersvAberdeenPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-04-17 | AberdeenvDundee UnitedPremiership · Scotland | 0–4 | Premiership · Scotland |
| 1999-04-10 | KilmarnockvAberdeenPremiership · Scotland | 4–2 | Premiership · Scotland |
| 1999-04-03 | AberdeenvDunfermlinePremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-03-20 | MotherwellvAberdeenPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-03-14 | AberdeenvCelticPremiership · Scotland | 1–5 | Premiership · Scotland |
| 1999-02-27 | HeartsvAberdeenPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-02-20 | Dundee UnitedvAberdeenPremiership · Scotland | 3–0 | Premiership · Scotland |
| 1999-02-06 | AberdeenvKilmarnockPremiership · Scotland | 2–1 | Premiership · Scotland |
| 1999-01-30 | AberdeenvRangersPremiership · Scotland | 2–4 | Premiership · Scotland |
| 1999-01-02 | St JohnstonevAberdeenPremiership · Scotland | 4–1 | Premiership · Scotland |