| 1999-11-27 | IpswichvCreweChampionship · England | 2–1 | Championship · England |
| 1999-11-24 | IpswichvWolvesChampionship · England | 1–0 | Championship · England |
| 1999-11-21 | NorwichvIpswichChampionship · England | 0–0 | Championship · England |
| 1999-11-12 | IpswichvTranmereChampionship · England | 0–0 | Championship · England |
| 1999-11-06 | BlackburnvIpswichChampionship · England | 2–2 | Championship · England |
| 1999-11-02 | HuddersfieldvIpswichChampionship · England | 3–1 | Championship · England |
| 1999-10-30 | IpswichvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1999-10-27 | Man CityvIpswichChampionship · England | 1–0 | Championship · England |
| 1999-10-23 | WalsallvIpswichChampionship · England | 0–1 | Championship · England |
| 1999-10-19 | IpswichvCharltonChampionship · England | 4–2 | Championship · England |
| 1999-10-16 | IpswichvQPRChampionship · England | 1–4 | Championship · England |
| 1999-10-02 | GrimsbyvIpswichChampionship · England | 2–1 | Championship · England |
| 1999-09-26 | IpswichvMan CityChampionship · England | 2–1 | Championship · England |
| 1999-09-18 | IpswichvBirminghamChampionship · England | 0–1 | Championship · England |
| 1999-09-11 | PortsmouthvIpswichChampionship · England | 1–1 | Championship · England |
| 1999-08-30 | IpswichvBarnsleyChampionship · England | 6–1 | Championship · England |
| 1999-08-28 | Sheffield UnitedvIpswichChampionship · England | 2–2 | Championship · England |
| 1999-08-21 | IpswichvBoltonChampionship · England | 1–0 | Championship · England |
| 1999-08-15 | SwindonvIpswichChampionship · England | 1–4 | Championship · England |
| 1999-08-07 | IpswichvNott'm ForestChampionship · England | 3–1 | Championship · England |
| 1999-05-09 | IpswichvSheffield UnitedChampionship · England | 4–1 | Championship · England |
| 1999-05-02 | BirminghamvIpswichChampionship · England | 1–0 | Championship · England |
| 1999-04-24 | IpswichvCreweChampionship · England | 1–2 | Championship · England |
| 1999-04-20 | IpswichvStockportChampionship · England | 1–0 | Championship · England |
| 1999-04-17 | BoltonvIpswichChampionship · England | 2–0 | Championship · England |
| 1999-04-11 | NorwichvIpswichChampionship · England | 0–0 | Championship · England |
| 1999-04-05 | IpswichvQPRChampionship · England | 3–1 | Championship · England |
| 1999-04-03 | SwindonvIpswichChampionship · England | 0–6 | Championship · England |
| 1999-03-20 | West BromvIpswichChampionship · England | 0–1 | Championship · England |
| 1999-03-13 | IpswichvHuddersfieldChampionship · England | 3–0 | Championship · England |
| 1999-03-09 | Crystal PalacevIpswichChampionship · England | 3–2 | Championship · England |
| 1999-03-06 | IpswichvTranmereChampionship · England | 1–0 | Championship · England |
| 1999-03-02 | IpswichvWatfordChampionship · England | 3–2 | Championship · England |
| 1999-02-27 | Bristol CityvIpswichChampionship · England | 0–1 | Championship · England |
| 1999-02-20 | IpswichvOxfordChampionship · England | 2–1 | Championship · England |
| 1999-02-13 | BradfordvIpswichChampionship · England | 0–0 | Championship · England |
| 1999-02-06 | BuryvIpswichChampionship · England | 0–3 | Championship · England |
| 1999-01-30 | IpswichvPort ValeChampionship · England | 1–0 | Championship · England |
| 1999-01-17 | SunderlandvIpswichChampionship · England | 2–1 | Championship · England |
| 1999-01-09 | IpswichvGrimsbyChampionship · England | 0–1 | Championship · England |
| 1998-12-28 | WolvesvIpswichChampionship · England | 1–0 | Championship · England |
| 1998-12-26 | IpswichvPortsmouthChampionship · England | 3–0 | Championship · England |
| 1998-12-20 | Sheffield UnitedvIpswichChampionship · England | 1–2 | Championship · England |
| 1998-12-12 | IpswichvBarnsleyChampionship · England | 0–2 | Championship · England |
| 1998-12-05 | IpswichvBirminghamChampionship · England | 1–0 | Championship · England |
| 1998-12-02 | QPRvIpswichChampionship · England | 1–1 | Championship · England |
| 1998-11-28 | CrewevIpswichChampionship · England | 0–3 | Championship · England |
| 1998-11-21 | IpswichvBoltonChampionship · England | 0–1 | Championship · England |
| 1998-11-14 | BarnsleyvIpswichChampionship · England | 0–1 | Championship · England |
| 1998-11-07 | HuddersfieldvIpswichChampionship · England | 2–2 | Championship · England |