| 1999-12-28 | WatfordvSouthamptonPremier League · England | 3–2 | Premier League · England |
| 1999-12-26 | SouthamptonvChelseaPremier League · England | 1–2 | Premier League · England |
| 1999-12-18 | SunderlandvSouthamptonPremier League · England | 2–0 | Premier League · England |
| 1999-12-04 | SouthamptonvCoventryPremier League · England | 0–0 | Premier League · England |
| 1999-11-28 | LeedsvSouthamptonPremier League · England | 1–0 | Premier League · England |
| 1999-11-20 | SouthamptonvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-11-06 | Aston VillavSouthamptonPremier League · England | 0–1 | Premier League · England |
| 1999-10-30 | WimbledonvSouthamptonPremier League · England | 1–1 | Premier League · England |
| 1999-10-23 | SouthamptonvLiverpoolPremier League · England | 1–1 | Premier League · England |
| 1999-10-16 | LeicestervSouthamptonPremier League · England | 2–1 | Premier League · England |
| 1999-10-04 | SouthamptonvDerbyPremier League · England | 3–3 | Premier League · England |
| 1999-09-25 | Man UnitedvSouthamptonPremier League · England | 3–3 | Premier League · England |
| 1999-09-18 | SouthamptonvArsenalPremier League · England | 0–1 | Premier League · England |
| 1999-09-11 | MiddlesbroughvSouthamptonPremier League · England | 3–2 | Premier League · England |
| 1999-08-28 | SouthamptonvSheffield WedsPremier League · England | 2–0 | Premier League · England |
| 1999-08-21 | EvertonvSouthamptonPremier League · England | 4–1 | Premier League · England |
| 1999-08-15 | SouthamptonvNewcastlePremier League · England | 4–2 | Premier League · England |
| 1999-08-11 | SouthamptonvLeedsPremier League · England | 0–3 | Premier League · England |
| 1999-08-07 | CoventryvSouthamptonPremier League · England | 0–1 | Premier League · England |
| 1999-05-16 | SouthamptonvEvertonPremier League · England | 2–0 | Premier League · England |
| 1999-05-08 | WimbledonvSouthamptonPremier League · England | 0–2 | Premier League · England |
| 1999-05-01 | SouthamptonvLeicesterPremier League · England | 2–1 | Premier League · England |
| 1999-04-24 | DerbyvSouthamptonPremier League · England | 0–0 | Premier League · England |
| 1999-04-17 | SouthamptonvBlackburnPremier League · England | 3–3 | Premier League · England |
| 1999-04-10 | Aston VillavSouthamptonPremier League · England | 3–0 | Premier League · England |
| 1999-04-05 | CoventryvSouthamptonPremier League · England | 1–0 | Premier League · England |
| 1999-04-03 | SouthamptonvArsenalPremier League · England | 0–0 | Premier League · England |
| 1999-03-20 | SouthamptonvSheffield WedsPremier League · England | 1–0 | Premier League · England |
| 1999-03-14 | MiddlesbroughvSouthamptonPremier League · England | 3–0 | Premier League · England |
| 1999-03-06 | SouthamptonvWest HamPremier League · England | 1–0 | Premier League · England |
| 1999-03-02 | TottenhamvSouthamptonPremier League · England | 3–0 | Premier League · England |
| 1999-02-27 | Man UnitedvSouthamptonPremier League · England | 2–1 | Premier League · England |
| 1999-02-20 | SouthamptonvNewcastlePremier League · England | 2–1 | Premier League · England |
| 1999-02-06 | ChelseavSouthamptonPremier League · England | 1–0 | Premier League · England |
| 1999-01-30 | SouthamptonvLeedsPremier League · England | 3–0 | Premier League · England |
| 1999-01-16 | LiverpoolvSouthamptonPremier League · England | 7–1 | Premier League · England |
| 1999-01-09 | SouthamptonvCharltonPremier League · England | 3–1 | Premier League · England |