| 2000-12-09 | Nott'm ForestvPortsmouthChampionship · England | 2–0 | Championship · England |
| 2000-12-02 | PortsmouthvNorwichChampionship · England | 2–0 | Championship · England |
| 2000-11-25 | BarnsleyvPortsmouthChampionship · England | 1–0 | Championship · England |
| 2000-11-18 | FulhamvPortsmouthChampionship · England | 3–1 | Championship · England |
| 2000-11-11 | PortsmouthvBlackburnChampionship · England | 2–2 | Championship · England |
| 2000-11-04 | QPRvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-10-28 | PortsmouthvBirminghamChampionship · England | 1–1 | Championship · England |
| 2000-10-24 | NorwichvPortsmouthChampionship · England | 0–0 | Championship · England |
| 2000-10-21 | Crystal PalacevPortsmouthChampionship · England | 2–3 | Championship · England |
| 2000-10-17 | PortsmouthvCreweChampionship · England | 2–1 | Championship · England |
| 2000-10-14 | PortsmouthvSheffield WedsChampionship · England | 2–1 | Championship · England |
| 2000-10-08 | StockportvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-09-30 | BurnleyvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-09-23 | PortsmouthvWest BromChampionship · England | 0–1 | Championship · England |
| 2000-09-16 | BoltonvPortsmouthChampionship · England | 2–0 | Championship · England |
| 2000-09-12 | PortsmouthvTranmereChampionship · England | 2–0 | Championship · England |
| 2000-09-09 | PortsmouthvWatfordChampionship · England | 1–3 | Championship · England |
| 2000-09-02 | PrestonvPortsmouthChampionship · England | 1–0 | Championship · England |
| 2000-08-28 | PortsmouthvWolvesChampionship · England | 3–1 | Championship · England |
| 2000-08-25 | GillinghamvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-08-19 | PortsmouthvGrimsbyChampionship · England | 1–1 | Championship · England |
| 2000-08-12 | Sheffield UnitedvPortsmouthChampionship · England | 2–0 | Championship · England |
| 2000-05-07 | PortsmouthvQPRChampionship · England | 1–3 | Championship · England |
| 2000-04-29 | WalsallvPortsmouthChampionship · England | 1–0 | Championship · England |
| 2000-04-24 | PortsmouthvMan CityChampionship · England | 2–2 | Championship · England |
| 2000-04-21 | CharltonvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-04-15 | BlackburnvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-04-08 | PortsmouthvNorwichChampionship · England | 2–1 | Championship · England |
| 2000-04-01 | Port ValevPortsmouthChampionship · England | 2–0 | Championship · England |
| 2000-03-25 | PortsmouthvSwindonChampionship · England | 4–1 | Championship · England |
| 2000-03-21 | PortsmouthvWest BromChampionship · England | 2–0 | Championship · England |
| 2000-03-18 | CrewevPortsmouthChampionship · England | 1–3 | Championship · England |
| 2000-03-11 | PortsmouthvNott'm ForestChampionship · England | 2–1 | Championship · England |
| 2000-03-07 | BirminghamvPortsmouthChampionship · England | 1–0 | Championship · England |
| 2000-03-04 | IpswichvPortsmouthChampionship · England | 0–1 | Championship · England |
| 2000-03-01 | PortsmouthvTranmereChampionship · England | 1–2 | Championship · England |
| 2000-02-22 | BoltonvPortsmouthChampionship · England | 3–0 | Championship · England |
| 2000-02-12 | PortsmouthvFulhamChampionship · England | 0–1 | Championship · England |
| 2000-02-05 | HuddersfieldvPortsmouthChampionship · England | 0–1 | Championship · England |
| 2000-01-29 | PortsmouthvBarnsleyChampionship · England | 3–0 | Championship · England |
| 2000-01-22 | StockportvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-01-15 | PortsmouthvWolvesChampionship · England | 2–3 | Championship · England |
| 2000-01-03 | NorwichvPortsmouthChampionship · England | 2–1 | Championship · England |
| 1999-12-28 | PortsmouthvBlackburnChampionship · England | 1–2 | Championship · England |
| 1999-12-26 | SwindonvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-12-18 | PortsmouthvPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-12-04 | Sheffield UnitedvPortsmouthChampionship · England | 1–0 | Championship · England |
| 1999-11-27 | PortsmouthvBoltonChampionship · England | 0–0 | Championship · England |
| 1999-11-24 | Nott'm ForestvPortsmouthChampionship · England | 2–0 | Championship · England |
| 1999-11-20 | PortsmouthvCreweChampionship · England | 0–2 | Championship · England |