| 1 | Sat 3 Aug 2019 | 1-0 v Burton AlbionBurton Albion 0-1 Ipswich Town | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 1-1 v SunderlandIpswich Town 1-1 Sunderland | Sky Bet League One |
| 3 | Tue 13 Aug 2019 | 1-3 v Luton TownLuton Town 3-1 Ipswich Town | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 2-2 v Peterborough UnitedPeterborough United 2-2 Ipswich Town | Sky Bet League One |
| 5 | Tue 20 Aug 2019 | 2-1 v AFC WimbledonIpswich Town 2-1 AFC Wimbledon | Sky Bet League One |
| 6 | Sat 24 Aug 2019 | 5-0 v Bolton WanderersBolton Wanderers 0-5 Ipswich Town | Sky Bet League One |
| 7 | Sat 31 Aug 2019 | 3-0 v Shrewsbury TownIpswich Town 3-0 Shrewsbury Town | Sky Bet League One |
| 8 | Sat 28 Sep 2019 | 4-1 v Tranmere RoversIpswich Town 4-1 Tranmere Rovers | Sky Bet League One |
| 9 | Sat 5 Oct 2019 | 1-0 v Fleetwood TownFleetwood Town 0-1 Ipswich Town | Sky Bet League One |
| 10 | Tue 8 Oct 2019 | 4-0 v GillinghamIpswich Town 4-0 Gillingham | Leasing.com Trophy Southern Group A |
| 11 | Sun 20 Oct 2019 | 0-2 v Accrington StanleyAccrington Stanley 2-0 Ipswich Town | Sky Bet League One |
| 12 | Wed 23 Oct 2019 | 0-2 v Rotherham UnitedIpswich Town 0-2 Rotherham United | Sky Bet League One |
| 13 | Sat 26 Oct 2019 | 3-1 v Southend UnitedSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 14 | Tue 5 Nov 2019 | 1-0 v RochdaleRochdale 0-1 Ipswich Town | Sky Bet League One |
| 15 | Sat 9 Nov 2019 | 1-1 v Lincoln CityIpswich Town 1-1 Lincoln City | Emirates FA Cup First Round |
| 16 | Sat 23 Nov 2019 | 2-2 v BlackpoolIpswich Town 2-2 Blackpool | Sky Bet League One |
| 17 | Sun 1 Dec 2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Emirates FA Cup Second Round |
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