| 1999-01-30 | BlackburnvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-01-30 | WimbledonvWest HamPremier League · England | 0–0 | Premier League · England |
| 1999-01-30 | CoventryvLiverpoolPremier League · England | 2–1 | Premier League · England |
| 1999-01-30 | MiddlesbroughvLeicesterPremier League · England | 0–0 | Premier League · England |
| 1999-01-30 | Sheffield WedsvDerbyPremier League · England | 0–1 | Premier League · England |
| 1999-01-18 | Aston VillavEvertonPremier League · England | 3–0 | Premier League · England |
| 1999-01-17 | CharltonvNewcastlePremier League · England | 2–2 | Premier League · England |
| 1999-01-16 | DerbyvBlackburnPremier League · England | 1–0 | Premier League · England |
| 1999-01-16 | TottenhamvWimbledonPremier League · England | 0–0 | Premier League · England |
| 1999-01-16 | West HamvSheffield WedsPremier League · England | 0–4 | Premier League · England |
| 1999-01-16 | LeicestervMan UnitedPremier League · England | 2–6 | Premier League · England |
| 1999-01-16 | ChelseavCoventryPremier League · England | 2–1 | Premier League · England |
| 1999-01-16 | Nott'm ForestvArsenalPremier League · England | 0–1 | Premier League · England |
| 1999-01-16 | LiverpoolvSouthamptonPremier League · England | 7–1 | Premier League · England |
| 1999-01-16 | LeedsvMiddlesbroughPremier League · England | 2–0 | Premier League · England |
| 1999-01-10 | Man UnitedvWest HamPremier League · England | 4–1 | Premier League · England |
| 1999-01-09 | EvertonvLeicesterPremier League · England | 0–0 | Premier League · England |
| 1999-01-09 | Sheffield WedsvTottenhamPremier League · England | 0–0 | Premier League · England |
| 1999-01-09 | CoventryvNott'm ForestPremier League · England | 4–0 | Premier League · England |
| 1999-01-09 | NewcastlevChelseaPremier League · England | 0–1 | Premier League · England |
| 1999-01-09 | BlackburnvLeedsPremier League · England | 1–0 | Premier League · England |
| 1999-01-09 | WimbledonvDerbyPremier League · England | 2–1 | Premier League · England |
| 1999-01-09 | SouthamptonvCharltonPremier League · England | 3–1 | Premier League · England |
| 1999-01-09 | MiddlesbroughvAston VillaPremier League · England | 0–0 | Premier League · England |
| 1999-01-09 | ArsenalvLiverpoolPremier League · England | 0–0 | Premier League · England |