| 1 | Sat 5 Sep 2020 | 11-2 v Bradford CityBolton Wanderers 1-2 Bradford City | Carabao Cup First Round North |
| 2 | Sat 19 Sep 2020 | 10-2 v Colchester UnitedColchester United 2-0 Bolton Wanderers | Sky Bet League Two |
| 3 | Sat 26 Sep 2020 | 10-2 v Newport CountyBolton Wanderers 0-2 Newport County | Sky Bet League Two |
| 4 | Sat 3 Oct 2020 | 12-1 v Harrogate TownHarrogate Town 1-2 Bolton Wanderers | Sky Bet League Two |
| 5 | Tue 6 Oct 2020 | 11-2 v Shrewsbury TownShrewsbury Town 2-1 Bolton Wanderers | Papa John’s Trophy Group 7 |
| 6 | Sat 10 Oct 2020 | 10-0 v Grimsby TownBolton Wanderers 0-0 Grimsby Town | Sky Bet League Two |
| 7 | Sat 17 Oct 2020 | 11-2 v Oldham AthleticBolton Wanderers 1-2 Oldham Athletic | Sky Bet League Two |
| 8 | Tue 20 Oct 2020 | 13-3 v BarrowBarrow 3-3 Bolton Wanderers | Sky Bet League Two |
| 9 | Sat 24 Oct 2020 | 11-1 v Cambridge UnitedCambridge United 1-1 Bolton Wanderers | Sky Bet League Two |
| 10 | Tue 27 Oct 2020 | 11-0 v Bradford CityBolton Wanderers 1-0 Bradford City | Sky Bet League Two |
| 11 | Sat 31 Oct 2020 | 10-4 v Leyton OrientLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 12 | Tue 3 Nov 2020 | 11-1 v Mansfield TownBolton Wanderers 1-1 Mansfield Town | Sky Bet League Two |
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