| 1 | Sat 10 Aug 2019 | 0-0 v Coventry CityBolton Wanderers 0-0 Coventry City | Sky Bet League One |
| 2 | Tue 13 Aug 2019 | 2-5 v RochdaleRochdale 5-2 Bolton Wanderers | Carabao Cup First Round |
| 3 | Sat 31 Aug 2019 | 0-5 v GillinghamGillingham 5-0 Bolton Wanderers | Sky Bet League One |
| 4 | Sat 14 Sep 2019 | 1-6 v Rotherham UnitedRotherham United 6-1 Bolton Wanderers | Sky Bet League One |
| 5 | Tue 17 Sep 2019 | 0-0 v Oxford UnitedBolton Wanderers 0-0 Oxford United | Sky Bet League One |
| 6 | Sat 21 Sep 2019 | 1-1 v SunderlandBolton Wanderers 1-1 Sunderland | Sky Bet League One |
| 7 | Sat 28 Sep 2019 | 0-1 v PortsmouthPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 8 | Tue 1 Oct 2019 | 1-1 v RochdaleRochdale 1-1 Bolton Wanderers | Leasing.com Trophy Northern Group F |
| 9 | Mon 7 Oct 2019 | 0-0 v BlackpoolBolton Wanderers 0-0 Blackpool | Sky Bet League One |
| 10 | Sat 19 Oct 2019 | 1-3 v RochdaleBolton Wanderers 1-3 Rochdale | Sky Bet League One |
| 11 | Sat 2 Nov 2019 | 2-1 v Fleetwood TownBolton Wanderers 2-1 Fleetwood Town | Sky Bet League One |
| 12 | Sat 9 Nov 2019 | 0-1 v Plymouth ArgyleBolton Wanderers 0-1 Plymouth Argyle | Emirates FA Cup First Round |
| 13 | Sat 16 Nov 2019 | 1-0 v Milton Keynes DonsBolton Wanderers 1-0 Milton Keynes Dons | Sky Bet League One |
| 14 | Sat 7 Dec 2019 | 2-2 v AFC WimbledonBolton Wanderers 2-2 AFC Wimbledon | Sky Bet League One |
| 15 | Tue 10 Dec 2019 | 0-2 v Accrington StanleyAccrington Stanley 2-0 Bolton Wanderers | Leasing.com Trophy Second Round |
| 16 | Wed 1 Jan 2020 | 3-4 v Burton AlbionBolton Wanderers 3-4 Burton Albion | Sky Bet League One |
| 17 | Tue 14 Jan 2020 | 1-5 v Lincoln CityLincoln City 5-1 Bolton Wanderers | Sky Bet League One |
| 18 | Sat 1 Feb 2020 | 2-0 v Tranmere RoversBolton Wanderers 2-0 Tranmere Rovers | Sky Bet League One |
| 19 | Sat 8 Feb 2020 | 1-2 v Coventry CityCoventry City 2-1 Bolton Wanderers | Sky Bet League One |
| 20 | Sat 15 Feb 2020 | 0-2 v Wycombe WanderersBolton Wanderers 0-2 Wycombe Wanderers | Sky Bet League One |
| 21 | Sat 22 Feb 2020 | 0-1 v Milton Keynes DonsMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
| 22 | Tue 25 Feb 2020 | 1-2 v BlackpoolBlackpool 2-1 Bolton Wanderers | Sky Bet League One |
| 23 | Sat 29 Feb 2020 | 0-0 v Accrington StanleyBolton Wanderers 0-0 Accrington Stanley | Sky Bet League One |
| 24 | Sat 7 Mar 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Bolton Wanderers | Sky Bet League One |
| 25 | Tue 10 Mar 2020 | 2-2 v Burton AlbionBurton Albion 2-2 Bolton Wanderers | Sky Bet League One |
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