| 1 | Sat 19 Oct 2019 | 1-3 v RochdaleBolton Wanderers 1-3 Rochdale | Sky Bet League One |
| 2 | Tue 22 Oct 2019 | 2-0 v Bristol RoversBristol Rovers 0-2 Bolton Wanderers | Sky Bet League One |
| 3 | Sat 2 Nov 2019 | 2-1 v Fleetwood TownBolton Wanderers 2-1 Fleetwood Town | Sky Bet League One |
| 4 | Sat 9 Nov 2019 | 0-1 v Plymouth ArgyleBolton Wanderers 0-1 Plymouth Argyle | Emirates FA Cup First Round |
| 5 | Sat 16 Nov 2019 | 1-0 v Milton Keynes DonsBolton Wanderers 1-0 Milton Keynes Dons | Sky Bet League One |
| 6 | Sat 23 Nov 2019 | 1-7 v Accrington StanleyAccrington Stanley 7-1 Bolton Wanderers | Sky Bet League One |
| 7 | Sat 7 Dec 2019 | 2-2 v AFC WimbledonBolton Wanderers 2-2 AFC Wimbledon | Sky Bet League One |
| 8 | Tue 10 Dec 2019 | 0-2 v Accrington StanleyAccrington Stanley 2-0 Bolton Wanderers | Leasing.com Trophy Second Round |
| 9 | Sat 21 Dec 2019 | 3-2 v Southend UnitedBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 10 | Thu 26 Dec 2019 | 0-0 v SunderlandSunderland 0-0 Bolton Wanderers | Sky Bet League One |
| 11 | Sun 29 Dec 2019 | 1-1 v Shrewsbury TownBolton Wanderers 1-1 Shrewsbury Town | Sky Bet League One |
| 12 | Wed 1 Jan 2020 | 3-4 v Burton AlbionBolton Wanderers 3-4 Burton Albion | Sky Bet League One |
| 13 | Sat 11 Jan 2020 | 0-2 v RochdaleRochdale 2-0 Bolton Wanderers | Sky Bet League One |
| 14 | Tue 14 Jan 2020 | 1-5 v Lincoln CityLincoln City 5-1 Bolton Wanderers | Sky Bet League One |
| 15 | Tue 11 Feb 2020 | 1-2 v Doncaster RoversDoncaster Rovers 2-1 Bolton Wanderers | Sky Bet League One |
| 16 | Sat 15 Feb 2020 | 0-2 v Wycombe WanderersBolton Wanderers 0-2 Wycombe Wanderers | Sky Bet League One |
| 17 | Sat 22 Feb 2020 | 0-1 v Milton Keynes DonsMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
| 18 | Tue 25 Feb 2020 | 1-2 v BlackpoolBlackpool 2-1 Bolton Wanderers | Sky Bet League One |
| 19 | Sat 29 Feb 2020 | 0-0 v Accrington StanleyBolton Wanderers 0-0 Accrington Stanley | Sky Bet League One |
| 20 | Sat 7 Mar 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Bolton Wanderers | Sky Bet League One |
| 21 | Tue 10 Mar 2020 | 2-2 v Burton AlbionBurton Albion 2-2 Bolton Wanderers | Sky Bet League One |
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