| 1 | Tue 13 Aug 2019 | 1-3 v Luton TownLuton Town 3-1 Ipswich Town | Carabao Cup First Round |
| 2 | Tue 8 Oct 2019 | 4-0 v GillinghamIpswich Town 4-0 Gillingham | Leasing.com Trophy Southern Group A |
| 3 | Sat 26 Oct 2019 | 3-1 v Southend UnitedSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 4 | Tue 5 Nov 2019 | 1-0 v RochdaleRochdale 0-1 Ipswich Town | Sky Bet League One |
| 5 | Sat 9 Nov 2019 | 1-1 v Lincoln CityIpswich Town 1-1 Lincoln City | Emirates FA Cup First Round |
| 6 | Sat 23 Nov 2019 | 2-2 v BlackpoolIpswich Town 2-2 Blackpool | Sky Bet League One |
| 7 | Sun 1 Dec 2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Emirates FA Cup Second Round |
| 8 | Sat 7 Dec 2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Sky Bet League One |
| 9 | Sat 21 Dec 2019 | 0-1 v PortsmouthPortsmouth 1-0 Ipswich Town | Sky Bet League One |
| 10 | Thu 26 Dec 2019 | 0-0 v GillinghamIpswich Town 0-0 Gillingham | Sky Bet League One |
| 11 | Sun 29 Dec 2019 | 3-5 v Lincoln CityLincoln City 5-3 Ipswich Town | Sky Bet League One |
| 12 | Wed 1 Jan 2020 | 1-1 v Wycombe WanderersWycombe Wanderers 1-1 Ipswich Town | Sky Bet League One |
| 13 | Sat 11 Jan 2020 | 4-1 v Accrington StanleyIpswich Town 4-1 Accrington Stanley | Sky Bet League One |
| 14 | Tue 14 Jan 2020 | 0-0 v Oxford UnitedOxford United 0-0 Ipswich Town | Sky Bet League One |
| 15 | Sat 18 Jan 2020 | 2-1 v Tranmere RoversTranmere Rovers 1-2 Ipswich Town | Sky Bet League One |
| 16 | Sat 25 Jan 2020 | 1-0 v Lincoln CityIpswich Town 1-0 Lincoln City | Sky Bet League One |
| 17 | Tue 28 Jan 2020 | 0-1 v Rotherham UnitedRotherham United 1-0 Ipswich Town | Sky Bet League One |
| 18 | Sat 7 Mar 2020 | 0-1 v Coventry CityIpswich Town 0-1 Coventry City | Sky Bet League One |
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