| 2019-12-29 | LincolnvIpswichLeague One · England | 5–3 | League One · England |
| 2019-12-26 | IpswichvGillinghamLeague One · England | 0–0 | League One · England |
| 2019-12-21 | PortsmouthvIpswichLeague One · England | 1–0 | League One · England |
| 2019-12-14 | IpswichvBristol RvsLeague One · England | 1–2 | League One · England |
| 2019-12-07 | CoventryvIpswichLeague One · England | 1–1 | League One · England |
| 2019-11-26 | IpswichvWycombeLeague One · England | 0–0 | League One · England |
| 2019-11-23 | IpswichvBlackpoolLeague One · England | 2–2 | League One · England |
| 2019-11-05 | RochdalevIpswichLeague One · England | 0–1 | League One · England |
| 2019-10-26 | SouthendvIpswichLeague One · England | 1–3 | League One · England |
| 2019-10-23 | IpswichvRotherhamLeague One · England | 0–2 | League One · England |
| 2019-10-20 | AccringtonvIpswichLeague One · England | 2–0 | League One · England |
| 2019-10-05 | Fleetwood TownvIpswichLeague One · England | 0–1 | League One · England |
| 2019-09-28 | IpswichvTranmereLeague One · England | 4–1 | League One · England |
| 2019-09-21 | GillinghamvIpswichLeague One · England | 0–1 | League One · England |
| 2019-09-17 | Milton Keynes DonsvIpswichLeague One · England | 0–1 | League One · England |
| 2019-09-14 | IpswichvDoncasterLeague One · England | 0–0 | League One · England |
| 2019-08-31 | IpswichvShrewsburyLeague One · England | 3–0 | League One · England |
| 2019-08-24 | BoltonvIpswichLeague One · England | 0–5 | League One · England |
| 2019-08-20 | IpswichvAFC WimbledonLeague One · England | 2–1 | League One · England |
| 2019-08-17 | PeterborovIpswichLeague One · England | 2–2 | League One · England |
| 2019-08-10 | IpswichvSunderlandLeague One · England | 1–1 | League One · England |
| 2019-08-03 | BurtonvIpswichLeague One · England | 0–1 | League One · England |
| 2019-05-05 | IpswichvLeedsChampionship · England | 3–2 | Championship · England |
| 2019-04-27 | Sheffield UnitedvIpswichChampionship · England | 2–0 | Championship · England |
| 2019-04-22 | IpswichvSwanseaChampionship · England | 0–1 | Championship · England |
| 2019-04-19 | PrestonvIpswichChampionship · England | 4–0 | Championship · England |
| 2019-04-13 | IpswichvBirminghamChampionship · England | 1–1 | Championship · England |
| 2019-04-10 | BrentfordvIpswichChampionship · England | 2–0 | Championship · England |
| 2019-04-06 | BoltonvIpswichChampionship · England | 1–2 | Championship · England |
| 2019-03-30 | IpswichvHullChampionship · England | 0–2 | Championship · England |
| 2019-03-16 | IpswichvNott'm ForestChampionship · England | 1–1 | Championship · England |
| 2019-03-12 | Bristol CityvIpswichChampionship · England | 1–1 | Championship · England |
| 2019-03-09 | West BromvIpswichChampionship · England | 1–1 | Championship · England |
| 2019-03-02 | IpswichvReadingChampionship · England | 1–2 | Championship · England |
| 2019-02-23 | WiganvIpswichChampionship · England | 1–1 | Championship · England |
| 2019-02-16 | IpswichvStokeChampionship · England | 1–1 | Championship · England |
| 2019-02-13 | IpswichvDerbyChampionship · England | 1–1 | Championship · England |
| 2019-02-10 | NorwichvIpswichChampionship · England | 3–0 | Championship · England |
| 2019-02-02 | IpswichvSheffield WedsChampionship · England | 0–1 | Championship · England |
| 2019-01-26 | Aston VillavIpswichChampionship · England | 2–1 | Championship · England |
| 2019-01-19 | BlackburnvIpswichChampionship · England | 2–0 | Championship · England |
| 2019-01-12 | IpswichvRotherhamChampionship · England | 1–0 | Championship · England |
| 2019-01-01 | IpswichvMillwallChampionship · England | 2–3 | Championship · England |