| 1 | Sat 3 Aug 2019 | 1-0 v Burton AlbionBurton Albion 0-1 Ipswich Town | Sky Bet League One |
| 2 | Tue 13 Aug 2019 | 1-3 v Luton TownLuton Town 3-1 Ipswich Town | Carabao Cup First Round |
| 3 | Tue 20 Aug 2019 | 2-1 v AFC WimbledonIpswich Town 2-1 AFC Wimbledon | Sky Bet League One |
| 4 | Sat 24 Aug 2019 | 5-0 v Bolton WanderersBolton Wanderers 0-5 Ipswich Town | Sky Bet League One |
| 5 | Tue 17 Sep 2019 | 1-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Ipswich Town | Sky Bet League One |
| 6 | Sat 21 Sep 2019 | 1-0 v GillinghamGillingham 0-1 Ipswich Town | Sky Bet League One |
| 7 | Sat 28 Sep 2019 | 4-1 v Tranmere RoversIpswich Town 4-1 Tranmere Rovers | Sky Bet League One |
| 8 | Sat 5 Oct 2019 | 1-0 v Fleetwood TownFleetwood Town 0-1 Ipswich Town | Sky Bet League One |
| 9 | Tue 8 Oct 2019 | 4-0 v GillinghamIpswich Town 4-0 Gillingham | Leasing.com Trophy Southern Group A |
| 10 | Wed 23 Oct 2019 | 0-2 v Rotherham UnitedIpswich Town 0-2 Rotherham United | Sky Bet League One |
| 11 | Sat 26 Oct 2019 | 3-1 v Southend UnitedSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 12 | Sat 9 Nov 2019 | 1-1 v Lincoln CityIpswich Town 1-1 Lincoln City | Emirates FA Cup First Round |
| 13 | Sun 1 Dec 2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Emirates FA Cup Second Round |
| 14 | Sat 7 Dec 2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Sky Bet League One |
| 15 | Sat 14 Dec 2019 | 1-2 v Bristol RoversIpswich Town 1-2 Bristol Rovers | Sky Bet League One |
| 16 | Sun 29 Dec 2019 | 3-5 v Lincoln CityLincoln City 5-3 Ipswich Town | Sky Bet League One |
| 17 | Wed 1 Jan 2020 | 1-1 v Wycombe WanderersWycombe Wanderers 1-1 Ipswich Town | Sky Bet League One |
| 18 | Sat 4 Jan 2020 | 1-2 v Exeter CityExeter City 2-1 Ipswich Town | Leasing.com Trophy Third Round |
| 19 | Sat 11 Jan 2020 | 4-1 v Accrington StanleyIpswich Town 4-1 Accrington Stanley | Sky Bet League One |
| 20 | Tue 14 Jan 2020 | 0-0 v Oxford UnitedOxford United 0-0 Ipswich Town | Sky Bet League One |
| 21 | Sat 18 Jan 2020 | 2-1 v Tranmere RoversTranmere Rovers 1-2 Ipswich Town | Sky Bet League One |
| 22 | Sat 25 Jan 2020 | 1-0 v Lincoln CityIpswich Town 1-0 Lincoln City | Sky Bet League One |
| 23 | Tue 28 Jan 2020 | 0-1 v Rotherham UnitedRotherham United 1-0 Ipswich Town | Sky Bet League One |
| 24 | Sat 8 Feb 2020 | 0-1 v SunderlandSunderland 1-0 Ipswich Town | Sky Bet League One |
| 25 | Tue 11 Feb 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Ipswich Town | Sky Bet League One |
| 26 | Tue 3 Mar 2020 | 0-1 v Fleetwood TownIpswich Town 0-1 Fleetwood Town | Sky Bet League One |
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