| 1 | Sat 3 Aug 2019 | 81-0 v FulhamBarnsley 1-0 Fulham | Sky Bet Championship |
| 2 | Sat 10 Aug 2019 | 8 0-2 v Sheffield WednesdaySheffield Wednesday 2-0 Barnsley | Sky Bet Championship |
| 3 | Tue 13 Aug 2019 | 80-3 v Carlisle UnitedBarnsley 0-3 Carlisle United | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 82-2 v Charlton AthleticBarnsley 2-2 Charlton Athletic | Sky Bet Championship |
| 5 | Tue 20 Aug 2019 | 80-2 v Birmingham CityBirmingham City 2-0 Barnsley | Sky Bet Championship |
| 6 | Sat 24 Aug 2019 | 81-3 v Luton TownBarnsley 1-3 Luton Town | Sky Bet Championship |
| 7 | Sat 21 Sep 2019 | 80-1 v Nottingham ForestNottingham Forest 1-0 Barnsley | Sky Bet Championship |
| 8 | Sat 5 Oct 2019 | 8 1-5 v Preston North EndPreston North End 5-1 Barnsley | Sky Bet Championship |
| 9 | Sat 19 Oct 2019 | 81-1 v Swansea CityBarnsley 1-1 Swansea City | Sky Bet Championship |
| 10 | Tue 22 Oct 2019 | 8 2-2 v West Bromwich AlbionWest Bromwich Albion 2-2 Barnsley | Sky Bet Championship |
| 11 | Sat 26 Oct 2019 | 81-2 v Huddersfield TownHuddersfield Town 2-1 Barnsley | Sky Bet Championship |
| 12 | Sat 9 Nov 2019 | 8 2-4 v Stoke CityBarnsley 2-4 Stoke City | Sky Bet Championship |
| 13 | Wed 27 Nov 2019 | 80-1 v MiddlesbroughMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
| 14 | Sat 14 Dec 2019 | 85-3 v Queens Park RangersBarnsley 5-3 Queens Park Rangers | Sky Bet Championship |
| 15 | Sat 11 Jan 2020 | 2-1 v AFC WimbledonPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 16 | Sat 18 Jan 2020 | 1-0 v Bolton WanderersBolton Wanderers 0-1 Portsmouth | Sky Bet League One |
| 17 | Tue 21 Jan 2020 | 2-1 v Scunthorpe UnitedPortsmouth 2-1 Scunthorpe United | Leasing.com Trophy Fourth Round |
| 18 | Tue 28 Jan 2020 | 2-0 v Lincoln CityLincoln City 0-2 Portsmouth | Sky Bet League One |
| 19 | Sat 1 Feb 2020 | 2-0 v SunderlandPortsmouth 2-0 Sunderland | Sky Bet League One |
| 20 | Sat 8 Feb 2020 | 2-0 v Tranmere RoversTranmere Rovers 0-2 Portsmouth | Sky Bet League One |
| 21 | Tue 11 Feb 2020 | 0-1 v Coventry CityCoventry City 1-0 Portsmouth | Sky Bet League One |
| 22 | Sat 15 Feb 2020 | 2-0 v Shrewsbury TownPortsmouth 2-0 Shrewsbury Town | Sky Bet League One |
| 23 | Tue 18 Feb 2020 | 3-2 v Exeter CityPortsmouth 3-2 Exeter City | Leasing.com Trophy Semi Final |
| 24 | Sat 22 Feb 2020 | 0-1 v Fleetwood TownFleetwood Town 1-0 Portsmouth | Sky Bet League One |
| 25 | Tue 25 Feb 2020 | 3-1 v Milton Keynes DonsPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 26 | Fri 28 Feb 2020 | 3-0 v RochdalePortsmouth 3-0 Rochdale | Sky Bet League One |
| 27 | Mon 2 Mar 2020 | 0-2 v ArsenalPortsmouth 0-2 Arsenal | Emirates FA Cup Fifth Round |
| 28 | Sat 7 Mar 2020 | 0-2 v Peterborough UnitedPeterborough United 2-0 Portsmouth | Sky Bet League One |
| 29 | Tue 10 Mar 2020 | 2-2 v Fleetwood TownPortsmouth 2-2 Fleetwood Town | Sky Bet League One |
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