| 1 | 10/8/2019 | 0-0 v Coventry CityBolton Wanderers 0-0 Coventry City | Sky Bet League One |
| 2 | 13/8/2019 | 2-5 v RochdaleRochdale 5-2 Bolton Wanderers | Carabao Cup First Round |
| 3 | 17/8/2019 | 0-5 v Tranmere RoversTranmere Rovers 5-0 Bolton Wanderers | Sky Bet League One |
| 4 | 24/8/2019 | 0-5 v Ipswich TownBolton Wanderers 0-5 Ipswich Town | Sky Bet League One |
| 5 | 31/8/2019 | 0-5 v GillinghamGillingham 5-0 Bolton Wanderers | Sky Bet League One |
| 6 | 14/9/2019 | 1-6 v Rotherham UnitedRotherham United 6-1 Bolton Wanderers | Sky Bet League One |
| 7 | 17/9/2019 | 0-0 v Oxford UnitedBolton Wanderers 0-0 Oxford United | Sky Bet League One |
| 8 | 21/9/2019 | 1-1 v SunderlandBolton Wanderers 1-1 Sunderland | Sky Bet League One |
| 9 | 28/9/2019 | 0-1 v PortsmouthPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 10 | 1/10/2019 | 1-1 v RochdaleRochdale 1-1 Bolton Wanderers | Checkatrade Trophy Northern Group F |
| 11 | 7/10/2019 | 0-0 v BlackpoolBolton Wanderers 0-0 Blackpool | Sky Bet League One |
| 12 | 19/10/2019 | 1-3 v RochdaleBolton Wanderers 1-3 Rochdale | Sky Bet League One |
| 13 | 22/10/2019 | 2-0 v Bristol RoversBristol Rovers 0-2 Bolton Wanderers | Sky Bet League One |
| 14 | 2/11/2019 | 2-1 v Fleetwood TownBolton Wanderers 2-1 Fleetwood Town | Sky Bet League One |
| 15 | 9/11/2019 | 0-1 v Plymouth ArgyleBolton Wanderers 0-1 Plymouth Argyle | Emirates FA Cup First Round |
| 16 | 16/11/2019 | 1-0 v Milton Keynes DonsBolton Wanderers 1-0 Milton Keynes Dons | Sky Bet League One |
| 17 | 23/11/2019 | 1-7 v Accrington StanleyAccrington Stanley 7-1 Bolton Wanderers | Sky Bet League One |
| 18 | 7/12/2019 | 2-2 v AFC WimbledonBolton Wanderers 2-2 AFC Wimbledon | Sky Bet League One |
| 19 | 10/12/2019 | 0-2 v Accrington StanleyAccrington Stanley 2-0 Bolton Wanderers | Checkatrade Trophy Second Round |
