| 1999-12-28 | SunderlandvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1999-12-26 | Man UnitedvBradfordPremier League · England | 4–0 | Premier League · England |
| 1999-12-18 | West HamvMan UnitedPremier League · England | 2–4 | Premier League · England |
| 1999-12-04 | Man UnitedvEvertonPremier League · England | 5–1 | Premier League · England |
| 1999-11-20 | DerbyvMan UnitedPremier League · England | 1–2 | Premier League · England |
| 1999-11-06 | Man UnitedvLeicesterPremier League · England | 2–0 | Premier League · England |
| 1999-10-30 | Man UnitedvAston VillaPremier League · England | 3–0 | Premier League · England |
| 1999-10-23 | TottenhamvMan UnitedPremier League · England | 3–1 | Premier League · England |
| 1999-10-16 | Man UnitedvWatfordPremier League · England | 4–1 | Premier League · England |
| 1999-10-03 | ChelseavMan UnitedPremier League · England | 5–0 | Premier League · England |
| 1999-09-25 | Man UnitedvSouthamptonPremier League · England | 3–3 | Premier League · England |
| 1999-09-18 | Man UnitedvWimbledonPremier League · England | 1–1 | Premier League · England |
| 1999-09-11 | LiverpoolvMan UnitedPremier League · England | 2–3 | Premier League · England |
| 1999-08-30 | Man UnitedvNewcastlePremier League · England | 5–1 | Premier League · England |
| 1999-08-25 | CoventryvMan UnitedPremier League · England | 1–2 | Premier League · England |
| 1999-08-22 | ArsenalvMan UnitedPremier League · England | 1–2 | Premier League · England |
| 1999-08-14 | Man UnitedvLeedsPremier League · England | 2–0 | Premier League · England |
| 1999-08-11 | Man UnitedvSheffield WedsPremier League · England | 4–0 | Premier League · England |
| 1999-08-08 | EvertonvMan UnitedPremier League · England | 1–1 | Premier League · England |
| 1999-05-16 | Man UnitedvTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-05-12 | BlackburnvMan UnitedPremier League · England | 0–0 | Premier League · England |
| 1999-05-09 | MiddlesbroughvMan UnitedPremier League · England | 0–1 | Premier League · England |
| 1999-05-05 | LiverpoolvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1999-05-01 | Man UnitedvAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-04-25 | LeedsvMan UnitedPremier League · England | 1–1 | Premier League · England |
| 1999-04-17 | Man UnitedvSheffield WedsPremier League · England | 3–0 | Premier League · England |
| 1999-04-03 | WimbledonvMan UnitedPremier League · England | 1–1 | Premier League · England |
| 1999-03-21 | Man UnitedvEvertonPremier League · England | 3–1 | Premier League · England |
| 1999-03-13 | NewcastlevMan UnitedPremier League · England | 1–2 | Premier League · England |
| 1999-02-27 | Man UnitedvSouthamptonPremier League · England | 2–1 | Premier League · England |
| 1999-02-20 | CoventryvMan UnitedPremier League · England | 0–1 | Premier League · England |
| 1999-02-17 | Man UnitedvArsenalPremier League · England | 1–1 | Premier League · England |
| 1999-02-06 | Nott'm ForestvMan UnitedPremier League · England | 1–8 | Premier League · England |
| 1999-02-02 | Man UnitedvDerbyPremier League · England | 1–0 | Premier League · England |
| 1999-01-31 | CharltonvMan UnitedPremier League · England | 0–1 | Premier League · England |
| 1999-01-16 | LeicestervMan UnitedPremier League · England | 2–6 | Premier League · England |
| 1999-01-10 | Man UnitedvWest HamPremier League · England | 4–1 | Premier League · England |