| 1 | 17/8/2019 | 0-1 v MillwallMillwall 1-0 Sheffield Wednesday | Sky Bet Championship |
| 2 | 24/8/2019 | 1-2 v Preston North EndPreston North End 2-1 Sheffield Wednesday | Sky Bet Championship |
| 3 | 31/8/2019 | 1-2 v Queens Park RangersSheffield Wednesday 1-2 Queens Park Rangers | Sky Bet Championship |
| 4 | 15/9/2019 | 2-0 v Huddersfield TownHuddersfield Town 0-2 Sheffield Wednesday | Sky Bet Championship |
| 5 | 21/9/2019 | 1-1 v FulhamSheffield Wednesday 1-1 Fulham | Sky Bet Championship |
| 6 | 24/9/2019 | 0-2 v EvertonSheffield Wednesday 0-2 Everton | Carabao Cup Third Round |
| 7 | 28/9/2019 | 4-1 v MiddlesbroughMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 8 | 1/10/2019 | 0-1 v Hull CityHull City 1-0 Sheffield Wednesday | Sky Bet Championship |
| 9 | 5/10/2019 | 1-0 v Wigan AthleticSheffield Wednesday 1-0 Wigan Athletic | Sky Bet Championship |
| 10 | 18/10/2019 | 1-1 v Cardiff CityCardiff City 1-1 Sheffield Wednesday | Sky Bet Championship |
| 11 | 22/10/2019 | 1-0 v Stoke CitySheffield Wednesday 1-0 Stoke City | Sky Bet Championship |
| 12 | 26/10/2019 | 0-0 v Leeds UnitedSheffield Wednesday 0-0 Leeds United | Sky Bet Championship |
| 13 | 2/11/2019 | 1-2 v Blackburn RoversBlackburn Rovers 2-1 Sheffield Wednesday | Sky Bet Championship |
| 14 | 9/11/2019 | 2-2 v Swansea CitySheffield Wednesday 2-2 Swansea City | Sky Bet Championship |
| 15 | 23/11/2019 | 1-2 v West Bromwich AlbionWest Bromwich Albion 2-1 Sheffield Wednesday | Sky Bet Championship |
| 16 | 27/11/2019 | 1-1 v Birmingham CitySheffield Wednesday 1-1 Birmingham City | Sky Bet Championship |
| 17 | 30/11/2019 | 3-1 v Charlton AthleticCharlton Athletic 1-3 Sheffield Wednesday | Sky Bet Championship |
