| 1999-11-14 | West BromvPortsmouthChampionship · England | 3–2 | Championship · England |
| 1999-11-09 | FulhamvPortsmouthChampionship · England | 1–0 | Championship · England |
| 1999-11-06 | PortsmouthvBirminghamChampionship · England | 2–2 | Championship · England |
| 1999-11-03 | Man CityvPortsmouthChampionship · England | 4–2 | Championship · England |
| 1999-10-30 | PortsmouthvCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-10-26 | GrimsbyvPortsmouthChampionship · England | 1–0 | Championship · England |
| 1999-10-23 | QPRvPortsmouthChampionship · England | 0–0 | Championship · England |
| 1999-10-19 | PortsmouthvWalsallChampionship · England | 5–1 | Championship · England |
| 1999-10-16 | PortsmouthvCharltonChampionship · England | 0–2 | Championship · England |
| 1999-10-02 | Crystal PalacevPortsmouthChampionship · England | 4–0 | Championship · England |
| 1999-09-25 | PortsmouthvGrimsbyChampionship · England | 1–2 | Championship · England |
| 1999-09-18 | TranmerevPortsmouthChampionship · England | 2–4 | Championship · England |
| 1999-09-11 | PortsmouthvIpswichChampionship · England | 1–1 | Championship · England |
| 1999-08-30 | PortsmouthvHuddersfieldChampionship · England | 0–0 | Championship · England |
| 1999-08-28 | BarnsleyvPortsmouthChampionship · England | 6–0 | Championship · England |
| 1999-08-21 | PortsmouthvStockportChampionship · England | 2–0 | Championship · England |
| 1999-08-14 | WolvesvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-08-07 | PortsmouthvSheffield UnitedChampionship · England | 2–0 | Championship · England |
| 1999-05-09 | PortsmouthvBoltonChampionship · England | 0–2 | Championship · England |
| 1999-05-01 | CrewevPortsmouthChampionship · England | 3–1 | Championship · England |
| 1999-04-24 | PortsmouthvStockportChampionship · England | 3–1 | Championship · England |
| 1999-04-17 | West BromvPortsmouthChampionship · England | 2–2 | Championship · England |
| 1999-04-10 | BradfordvPortsmouthChampionship · England | 2–1 | Championship · England |
| 1999-04-05 | PortsmouthvBristol CityChampionship · England | 0–1 | Championship · England |
| 1999-04-03 | WolvesvPortsmouthChampionship · England | 2–0 | Championship · England |
| 1999-03-28 | PortsmouthvBarnsleyChampionship · England | 1–3 | Championship · England |
| 1999-03-20 | NorwichvPortsmouthChampionship · England | 0–0 | Championship · England |
| 1999-03-13 | PortsmouthvCrystal PalaceChampionship · England | 1–1 | Championship · England |
| 1999-03-09 | PortsmouthvSheffield UnitedChampionship · England | 1–0 | Championship · England |
| 1999-03-06 | BirminghamvPortsmouthChampionship · England | 4–1 | Championship · England |
| 1999-03-02 | SunderlandvPortsmouthChampionship · England | 2–0 | Championship · England |
| 1999-02-27 | PortsmouthvPort ValeChampionship · England | 4–0 | Championship · England |
| 1999-02-20 | SwindonvPortsmouthChampionship · England | 3–3 | Championship · England |
| 1999-02-13 | PortsmouthvBuryChampionship · England | 2–1 | Championship · England |
| 1999-02-06 | PortsmouthvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | QPRvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-01-16 | PortsmouthvHuddersfieldChampionship · England | 1–0 | Championship · England |
| 1999-01-09 | WatfordvPortsmouthChampionship · England | 0–0 | Championship · England |
| 1998-12-28 | PortsmouthvOxfordChampionship · England | 2–2 | Championship · England |
| 1998-12-26 | IpswichvPortsmouthChampionship · England | 3–0 | Championship · England |
| 1998-12-19 | BoltonvPortsmouthChampionship · England | 3–1 | Championship · England |
| 1998-12-13 | PortsmouthvGrimsbyChampionship · England | 0–1 | Championship · England |
| 1998-12-05 | PortsmouthvCreweChampionship · England | 2–0 | Championship · England |
| 1998-11-28 | StockportvPortsmouthChampionship · England | 2–0 | Championship · England |
| 1998-11-21 | PortsmouthvWest BromChampionship · England | 2–1 | Championship · England |
| 1998-11-14 | GrimsbyvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1998-11-10 | PortsmouthvNorwichChampionship · England | 1–2 | Championship · England |
| 1998-11-07 | Crystal PalacevPortsmouthChampionship · England | 4–1 | Championship · England |
| 1998-10-24 | BarnsleyvPortsmouthChampionship · England | 2–1 | Championship · England |
| 1998-10-20 | PortsmouthvBradfordChampionship · England | 2–4 | Championship · England |