| 1 | Sat 14 Sep 2019 | 1-6 v Rotherham UnitedRotherham United 6-1 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 17 Sep 2019 | 0-0 v Oxford UnitedBolton Wanderers 0-0 Oxford United | Sky Bet League One |
| 3 | Sat 21 Sep 2019 | 1-1 v SunderlandBolton Wanderers 1-1 Sunderland | Sky Bet League One |
| 4 | Sat 28 Sep 2019 | 0-1 v PortsmouthPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 5 | Tue 1 Oct 2019 | 1-1 v RochdaleRochdale 1-1 Bolton Wanderers | Leasing.com Trophy Northern Group F |
| 6 | Mon 7 Oct 2019 | 0-0 v BlackpoolBolton Wanderers 0-0 Blackpool | Sky Bet League One |
| 7 | Sat 19 Oct 2019 | 1-3 v RochdaleBolton Wanderers 1-3 Rochdale | Sky Bet League One |
| 8 | Tue 22 Oct 2019 | 2-0 v Bristol RoversBristol Rovers 0-2 Bolton Wanderers | Sky Bet League One |
| 9 | Sat 22 Feb 2020 | 0-1 v Milton Keynes DonsMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
| 10 | Tue 25 Feb 2020 | 1-2 v BlackpoolBlackpool 2-1 Bolton Wanderers | Sky Bet League One |
| 11 | Sat 29 Feb 2020 | 0-0 v Accrington StanleyBolton Wanderers 0-0 Accrington Stanley | Sky Bet League One |
| 12 | Sat 7 Mar 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Bolton Wanderers | Sky Bet League One |
| 13 | Tue 10 Mar 2020 | 2-2 v Burton AlbionBurton Albion 2-2 Bolton Wanderers | Sky Bet League One |
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