| 1 | Sat 10 Aug 2019 | 0-0 v Coventry CityBolton Wanderers 0-0 Coventry City | Sky Bet League One |
| 2 | Sat 17 Aug 2019 | 0-5 v Tranmere RoversTranmere Rovers 5-0 Bolton Wanderers | Sky Bet League One |
| 3 | Sat 24 Aug 2019 | 0-5 v Ipswich TownBolton Wanderers 0-5 Ipswich Town | Sky Bet League One |
| 4 | Sat 31 Aug 2019 | 0-5 v GillinghamGillingham 5-0 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 | Sat 19 Oct 2019 | 1-3 v RochdaleBolton Wanderers 1-3 Rochdale | Sky Bet League One |
| 7 | Sat 2 Nov 2019 | 2-1 v Fleetwood TownBolton Wanderers 2-1 Fleetwood Town | Sky Bet League One |
| 8 | Sat 9 Nov 2019 | 0-1 v Plymouth ArgyleBolton Wanderers 0-1 Plymouth Argyle | Emirates FA Cup First Round |
| 9 | Sat 23 Nov 2019 | 1-7 v Accrington StanleyAccrington Stanley 7-1 Bolton Wanderers | Sky Bet League One |
| 10 | Sat 7 Dec 2019 | 2-2 v AFC WimbledonBolton Wanderers 2-2 AFC Wimbledon | Sky Bet League One |
| 11 | Tue 10 Dec 2019 | 0-2 v Accrington StanleyAccrington Stanley 2-0 Bolton Wanderers | Leasing.com Trophy Second Round |
| 12 | Sat 21 Dec 2019 | 3-2 v Southend UnitedBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 13 | Sun 29 Dec 2019 | 1-1 v Shrewsbury TownBolton Wanderers 1-1 Shrewsbury Town | Sky Bet League One |
| 14 | Sat 11 Jan 2020 | 0-2 v RochdaleRochdale 2-0 Bolton Wanderers | Sky Bet League One |
| 15 | Sat 22 Feb 2020 | 0-1 v Milton Keynes DonsMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
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