| 1 | 3/8/2019 | 1-0 v Burton AlbionBurton Albion 0-1 Ipswich Town | Sky Bet League One |
| 2 | 10/8/2019 | 1-1 v SunderlandIpswich Town 1-1 Sunderland | Sky Bet League One |
| 3 | 17/8/2019 | 2-2 v Peterborough UnitedPeterborough United 2-2 Ipswich Town | Sky Bet League One |
| 4 | 20/8/2019 | 2-1 v AFC WimbledonIpswich Town 2-1 AFC Wimbledon | Sky Bet League One |
| 5 | 24/8/2019 | 5-0 v Bolton WanderersBolton Wanderers 0-5 Ipswich Town | Sky Bet League One |
| 6 | 31/8/2019 | 3-0 v Shrewsbury TownIpswich Town 3-0 Shrewsbury Town | Sky Bet League One |
| 7 | 14/9/2019 | 0-0 v Doncaster RoversIpswich Town 0-0 Doncaster Rovers | Sky Bet League One |
| 8 | 17/9/2019 | 1-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Ipswich Town | Sky Bet League One |
| 9 | 21/9/2019 | 1-0 v GillinghamGillingham 0-1 Ipswich Town | Sky Bet League One |
| 10 | 28/9/2019 | 4-1 v Tranmere RoversIpswich Town 4-1 Tranmere Rovers | Sky Bet League One |
| 11 | 5/10/2019 | 1-0 v Fleetwood TownFleetwood Town 0-1 Ipswich Town | Sky Bet League One |
| 12 | 23/10/2019 | 0-2 v Rotherham UnitedIpswich Town 0-2 Rotherham United | Sky Bet League One |
| 13 | 26/10/2019 | 3-1 v Southend UnitedSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 14 | 5/11/2019 | 1-0 v RochdaleRochdale 0-1 Ipswich Town | Sky Bet League One |
| 15 | 9/11/2019 | 1-1 v Lincoln CityIpswich Town 1-1 Lincoln City | Emirates FA Cup First Round |
| 16 | 1/12/2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Emirates FA Cup Second Round |
| 17 | 10/12/2019 | 1-2 v Coventry CityIpswich Town 1-2 Coventry City | Emirates FA Cup Second Round Replay |
