| 1 | Tue 8 Oct 2019 | 224-0 v GillinghamIpswich Town 4-0 Gillingham | Leasing.com Trophy Southern Group A |
| 2 | Sun 20 Oct 2019 | 22 0-2 v Accrington StanleyAccrington Stanley 2-0 Ipswich Town | Sky Bet League One |
| 3 | Sat 9 Nov 2019 | 221-1 v Lincoln CityIpswich Town 1-1 Lincoln City | Emirates FA Cup First Round |
| 4 | Tue 10 Dec 2019 | 221-2 v Coventry CityIpswich Town 1-2 Coventry City | Emirates FA Cup Second Round Replay |
| 5 | Sat 21 Dec 2019 | 22 0-1 v PortsmouthPortsmouth 1-0 Ipswich Town | Sky Bet League One |
| 6 | Thu 26 Dec 2019 | 22 0-0 v GillinghamIpswich Town 0-0 Gillingham | Sky Bet League One |
| 7 | Sat 4 Jan 2020 | 22 1-2 v Exeter CityExeter City 2-1 Ipswich Town | Leasing.com Trophy Third Round |
| 8 | Sat 11 Jan 2020 | 0-2 v RochdaleRochdale 2-0 Bolton Wanderers | Sky Bet League One |
| 9 | Tue 14 Jan 2020 | 1-5 v Lincoln CityLincoln City 5-1 Bolton Wanderers | Sky Bet League One |
| 10 | Sat 1 Feb 2020 | 2-0 v Tranmere RoversBolton Wanderers 2-0 Tranmere Rovers | Sky Bet League One |
| 11 | Sat 8 Feb 2020 | 1-2 v Coventry CityCoventry City 2-1 Bolton Wanderers | Sky Bet League One |
| 12 | Sat 15 Feb 2020 | 0-2 v Wycombe WanderersBolton Wanderers 0-2 Wycombe Wanderers | Sky Bet League One |
| 13 | Sat 22 Feb 2020 | 0-1 v Milton Keynes DonsMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
| 14 | Tue 25 Feb 2020 | 1-2 v BlackpoolBlackpool 2-1 Bolton Wanderers | Sky Bet League One |
| 15 | Sat 29 Feb 2020 | 0-0 v Accrington StanleyBolton Wanderers 0-0 Accrington Stanley | Sky Bet League One |
| 16 | Sat 7 Mar 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Bolton Wanderers | Sky Bet League One |
| 17 | Tue 10 Mar 2020 | 2-2 v Burton AlbionBurton Albion 2-2 Bolton Wanderers | Sky Bet League One |
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