| 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 | Sat 17 Aug 2019 | 2-2 v Peterborough UnitedPeterborough United 2-2 Ipswich Town | Sky Bet League One |
| 4 | Tue 20 Aug 2019 | 2-1 v AFC WimbledonIpswich Town 2-1 AFC Wimbledon | Sky Bet League One |
| 5 | Tue 8 Oct 2019 | 4-0 v GillinghamIpswich Town 4-0 Gillingham | Leasing.com Trophy Southern Group A |
| 6 | Sat 9 Nov 2019 | 1-1 v Lincoln CityIpswich Town 1-1 Lincoln City | Emirates FA Cup First Round |
| 7 | Sat 23 Nov 2019 | 2-2 v BlackpoolIpswich Town 2-2 Blackpool | Sky Bet League One |
| 8 | Sun 1 Dec 2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Emirates FA Cup Second Round |
| 9 | Sat 7 Dec 2019 | 1-1 v Coventry CityCoventry City 1-1 Ipswich Town | Sky Bet League One |
| 10 | Sat 21 Dec 2019 | 0-1 v PortsmouthPortsmouth 1-0 Ipswich Town | Sky Bet League One |
| 11 | Thu 26 Dec 2019 | 0-0 v GillinghamIpswich Town 0-0 Gillingham | Sky Bet League One |
| 12 | Sun 29 Dec 2019 | 3-5 v Lincoln CityLincoln City 5-3 Ipswich Town | Sky Bet League One |
| 13 | Sat 8 Feb 2020 | 0-1 v SunderlandSunderland 1-0 Ipswich Town | Sky Bet League One |
| 14 | Tue 11 Feb 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Ipswich Town | Sky Bet League One |
| 15 | Tue 3 Mar 2020 | 0-1 v Fleetwood TownIpswich Town 0-1 Fleetwood Town | Sky Bet League One |
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