| 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 17 Aug 2019 | 0-5 v Tranmere RoversTranmere Rovers 5-0 Bolton Wanderers | Sky Bet League One |
| 4 | Sat 24 Aug 2019 | 0-5 v Ipswich TownBolton Wanderers 0-5 Ipswich Town | Sky Bet League One |
| 5 | Sat 31 Aug 2019 | 0-5 v GillinghamGillingham 5-0 Bolton Wanderers | Sky Bet League One |
| 6 | Sat 14 Sep 2019 | 1-6 v Rotherham UnitedRotherham United 6-1 Bolton Wanderers | Sky Bet League One |
| 7 | Mon 7 Oct 2019 | 0-0 v BlackpoolBolton Wanderers 0-0 Blackpool | Sky Bet League One |
| 8 | Sat 7 Dec 2019 | 2-2 v AFC WimbledonBolton Wanderers 2-2 AFC Wimbledon | Sky Bet League One |
| 9 | Tue 10 Dec 2019 | 0-2 v Accrington StanleyAccrington Stanley 2-0 Bolton Wanderers | Leasing.com Trophy Second Round |
| 10 | Sat 21 Dec 2019 | 3-2 v Southend UnitedBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 11 | Thu 26 Dec 2019 | 0-0 v SunderlandSunderland 0-0 Bolton Wanderers | Sky Bet League One |
| 12 | Sun 29 Dec 2019 | 1-1 v Shrewsbury TownBolton Wanderers 1-1 Shrewsbury Town | Sky Bet League One |
| 13 | Wed 1 Jan 2020 | 3-4 v Burton AlbionBolton Wanderers 3-4 Burton Albion | Sky Bet League One |
| 14 | Sat 11 Jan 2020 | 0-2 v RochdaleRochdale 2-0 Bolton Wanderers | Sky Bet League One |
| 15 | Tue 14 Jan 2020 | 1-5 v Lincoln CityLincoln City 5-1 Bolton Wanderers | Sky Bet League One |
| 16 | Sat 1 Feb 2020 | 2-0 v Tranmere RoversBolton Wanderers 2-0 Tranmere Rovers | Sky Bet League One |
| 17 | Sat 7 Mar 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Bolton Wanderers | Sky Bet League One |
| 18 | Tue 10 Mar 2020 | 2-2 v Burton AlbionBurton Albion 2-2 Bolton Wanderers | Sky Bet League One |
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