| 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 | Sat 2 Nov 2019 | 2-1 v Fleetwood TownBolton Wanderers 2-1 Fleetwood Town | Sky Bet League One |
| 9 | Sat 16 Nov 2019 | 1-0 v Milton Keynes DonsBolton Wanderers 1-0 Milton Keynes Dons | Sky Bet League One |
| 10 | Sat 23 Nov 2019 | 1-7 v Accrington StanleyAccrington Stanley 7-1 Bolton Wanderers | Sky Bet League One |
| 11 | Sat 7 Dec 2019 | 2-2 v AFC WimbledonBolton Wanderers 2-2 AFC Wimbledon | Sky Bet League One |
| 12 | Tue 10 Dec 2019 | 0-2 v Accrington StanleyAccrington Stanley 2-0 Bolton Wanderers | Leasing.com Trophy Second Round |
| 13 | Sat 21 Dec 2019 | 3-2 v Southend UnitedBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 14 | Thu 26 Dec 2019 | 0-0 v SunderlandSunderland 0-0 Bolton Wanderers | Sky Bet League One |
| 15 | Sun 29 Dec 2019 | 1-1 v Shrewsbury TownBolton Wanderers 1-1 Shrewsbury Town | Sky Bet League One |
| 16 | Wed 1 Jan 2020 | 3-4 v Burton AlbionBolton Wanderers 3-4 Burton Albion | Sky Bet League One |
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