| 1999-11-20 | LeicestervWimbledonPremier League · England | 2–1 | Premier League · England |
| 1999-11-20 | SouthamptonvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-11-20 | SunderlandvLiverpoolPremier League · England | 0–2 | Premier League · England |
| 1999-11-20 | WatfordvNewcastlePremier League · England | 1–1 | Premier League · England |
| 1999-11-20 | ArsenalvMiddlesbroughPremier League · England | 5–1 | Premier League · England |
| 1999-11-20 | EvertonvChelseaPremier League · England | 1–1 | Premier League · England |
| 1999-11-20 | DerbyvMan UnitedPremier League · England | 1–2 | Premier League · England |
| 1999-11-20 | LeedsvBradfordPremier League · England | 2–1 | Premier League · England |
| 1999-11-07 | WimbledonvLeedsPremier League · England | 2–0 | Premier League · England |
| 1999-11-07 | TottenhamvArsenalPremier League · England | 2–1 | Premier League · England |
| 1999-11-07 | NewcastlevEvertonPremier League · England | 1–1 | Premier League · England |
| 1999-11-07 | ChelseavWest HamPremier League · England | 0–0 | Premier League · England |
| 1999-11-06 | LiverpoolvDerbyPremier League · England | 2–0 | Premier League · England |
| 1999-11-06 | Sheffield WedsvWatfordPremier League · England | 2–2 | Premier League · England |
| 1999-11-06 | MiddlesbroughvSunderlandPremier League · England | 1–1 | Premier League · England |
| 1999-11-06 | Man UnitedvLeicesterPremier League · England | 2–0 | Premier League · England |
| 1999-11-06 | BradfordvCoventryPremier League · England | 1–1 | Premier League · England |
| 1999-11-06 | Aston VillavSouthamptonPremier League · England | 0–1 | Premier League · England |
| 1999-11-01 | LiverpoolvBradfordPremier League · England | 3–1 | Premier League · England |
| 1999-10-31 | SunderlandvTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-10-31 | CoventryvWatfordPremier League · England | 4–0 | Premier League · England |
| 1999-10-30 | DerbyvChelseaPremier League · England | 3–1 | Premier League · England |
| 1999-10-30 | LeicestervSheffield WedsPremier League · England | 3–0 | Premier League · England |
| 1999-10-30 | LeedsvWest HamPremier League · England | 1–0 | Premier League · England |
| 1999-10-30 | MiddlesbroughvEvertonPremier League · England | 2–1 | Premier League · England |
| 1999-10-30 | Man UnitedvAston VillaPremier League · England | 3–0 | Premier League · England |
| 1999-10-30 | WimbledonvSouthamptonPremier League · England | 1–1 | Premier League · England |
| 1999-10-30 | ArsenalvNewcastlePremier League · England | 0–0 | Premier League · England |
| 1999-10-27 | LiverpoolvWest HamPremier League · England | 1–0 | Premier League · England |
| 1999-10-25 | NewcastlevDerbyPremier League · England | 2–0 | Premier League · England |
| 1999-10-24 | West HamvSunderlandPremier League · England | 1–1 | Premier League · England |
| 1999-10-24 | WatfordvMiddlesbroughPremier League · England | 1–3 | Premier League · England |
| 1999-10-24 | EvertonvLeedsPremier League · England | 4–4 | Premier League · England |
| 1999-10-23 | BradfordvLeicesterPremier League · England | 3–1 | Premier League · England |
| 1999-10-23 | SouthamptonvLiverpoolPremier League · England | 1–1 | Premier League · England |
| 1999-10-23 | Sheffield WedsvCoventryPremier League · England | 0–0 | Premier League · England |
| 1999-10-23 | ChelseavArsenalPremier League · England | 2–3 | Premier League · England |
| 1999-10-23 | Aston VillavWimbledonPremier League · England | 1–1 | Premier League · England |
| 1999-10-23 | TottenhamvMan UnitedPremier League · England | 3–1 | Premier League · England |
| 1999-10-18 | SunderlandvAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-10-17 | MiddlesbroughvWest HamPremier League · England | 2–0 | Premier League · England |
| 1999-10-16 | WimbledonvBradfordPremier League · England | 3–2 | Premier League · England |
| 1999-10-16 | LiverpoolvChelseaPremier League · England | 1–0 | Premier League · England |
| 1999-10-16 | CoventryvNewcastlePremier League · England | 4–1 | Premier League · England |
| 1999-10-16 | LeedsvSheffield WedsPremier League · England | 2–0 | Premier League · England |
| 1999-10-16 | LeicestervSouthamptonPremier League · England | 2–1 | Premier League · England |
| 1999-10-16 | DerbyvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-10-16 | ArsenalvEvertonPremier League · England | 4–1 | Premier League · England |
| 1999-10-16 | Man UnitedvWatfordPremier League · England | 4–1 | Premier League · England |
| 1999-10-04 | SouthamptonvDerbyPremier League · England | 3–3 | Premier League · England |