| 1 | Sat 10 Aug 2019 | 2-0 v BarnsleySheffield Wednesday 2-0 Barnsley | Sky Bet Championship |
| 2 | Sat 17 Aug 2019 | 0-1 v MillwallMillwall 1-0 Sheffield Wednesday | Sky Bet Championship |
| 3 | Tue 20 Aug 2019 | 1-0 v Luton TownSheffield Wednesday 1-0 Luton Town | Sky Bet Championship |
| 4 | Sat 24 Aug 2019 | 1-2 v Preston North EndPreston North End 2-1 Sheffield Wednesday | Sky Bet Championship |
| 5 | Sat 31 Aug 2019 | 1-2 v Queens Park RangersSheffield Wednesday 1-2 Queens Park Rangers | Sky Bet Championship |
| 6 | Sun 15 Sep 2019 | 2-0 v Huddersfield TownHuddersfield Town 0-2 Sheffield Wednesday | Sky Bet Championship |
| 7 | Sat 21 Sep 2019 | 1-1 v FulhamSheffield Wednesday 1-1 Fulham | Sky Bet Championship |
| 8 | Tue 24 Sep 2019 | 0-2 v EvertonSheffield Wednesday 0-2 Everton | Carabao Cup Third Round |
| 9 | Tue 1 Oct 2019 | 0-1 v Hull CityHull City 1-0 Sheffield Wednesday | Sky Bet Championship |
| 10 | Sat 5 Oct 2019 | 1-0 v Wigan AthleticSheffield Wednesday 1-0 Wigan Athletic | Sky Bet Championship |
| 11 | Fri 18 Oct 2019 | 1-1 v Cardiff CityCardiff City 1-1 Sheffield Wednesday | Sky Bet Championship |
| 12 | Sat 2 Nov 2019 | 1-2 v Blackburn RoversBlackburn Rovers 2-1 Sheffield Wednesday | Sky Bet Championship |
| 13 | Sat 9 Nov 2019 | 2-2 v Swansea CitySheffield Wednesday 2-2 Swansea City | Sky Bet Championship |
| 14 | Sat 23 Nov 2019 | 1-2 v West Bromwich AlbionWest Bromwich Albion 2-1 Sheffield Wednesday | Sky Bet Championship |
| 15 | Sat 30 Nov 2019 | 3-1 v Charlton AthleticCharlton Athletic 1-3 Sheffield Wednesday | Sky Bet Championship |
| 16 | Sat 7 Dec 2019 | 2-1 v BrentfordSheffield Wednesday 2-1 Brentford | Sky Bet Championship |
| 17 | Wed 11 Dec 2019 | 1-1 v Derby CountyDerby County 1-1 Sheffield Wednesday | Sky Bet Championship |
| 18 | Thu 26 Dec 2019 | 2-3 v Stoke CityStoke City 3-2 Sheffield Wednesday | Sky Bet Championship |
| 19 | Sun 29 Dec 2019 | 1-2 v Cardiff CitySheffield Wednesday 1-2 Cardiff City | Sky Bet Championship |
| 20 | Wed 1 Jan 2020 | 0-1 v Hull CitySheffield Wednesday 0-1 Hull City | Sky Bet Championship |
| 21 | Sat 4 Jan 2020 | 1-0 v Brighton & Hove AlbionBrighton & Hove Albion 0-1 Sheffield Wednesday | Emirates FA Cup Third Round |
| 22 | Sat 11 Jan 2020 | 2-0 v Leeds UnitedLeeds United 0-2 Sheffield Wednesday | Sky Bet Championship |
| 23 | Sat 18 Jan 2020 | 0-5 v Blackburn RoversSheffield Wednesday 0-5 Blackburn Rovers | Sky Bet Championship |
| 24 | Fri 24 Jan 2020 | 2-1 v Queens Park RangersQueens Park Rangers 1-2 Sheffield Wednesday | Emirates FA Cup Fourth Round |
| 25 | Sat 1 Feb 2020 | 0-0 v MillwallSheffield Wednesday 0-0 Millwall | Sky Bet Championship |
| 26 | Wed 12 Feb 2020 | 0-1 v Luton TownLuton Town 1-0 Sheffield Wednesday | Sky Bet Championship |
| 27 | Sat 15 Feb 2020 | 0-3 v ReadingSheffield Wednesday 0-3 Reading | Sky Bet Championship |
| 28 | Sat 22 Feb 2020 | 3-3 v Birmingham CityBirmingham City 3-3 Sheffield Wednesday | Sky Bet Championship |
| 29 | Wed 26 Feb 2020 | 1-0 v Charlton AthleticSheffield Wednesday 1-0 Charlton Athletic | Sky Bet Championship |
| 30 | Sat 29 Feb 2020 | 1-3 v Derby CountySheffield Wednesday 1-3 Derby County | Sky Bet Championship |
| 31 | Wed 4 Mar 2020 | 0-1 v Manchester CitySheffield Wednesday 0-1 Manchester City | Emirates FA Cup Fifth Round |
| 32 | Sat 7 Mar 2020 | 0-5 v BrentfordBrentford 5-0 Sheffield Wednesday | Sky Bet Championship |
| 33 | Sat 20 Jun 2020 | 141-1 v Nottingham ForestSheffield Wednesday 1-1 Nottingham Forest | Sky Bet Championship |
| 34 | Sun 28 Jun 2020 | 142-1 v Bristol CityBristol City 1-2 Sheffield Wednesday | Sky Bet Championship |
| 35 | Wed 1 Jul 2020 | 140-3 v West Bromwich AlbionSheffield Wednesday 0-3 West Bromwich Albion | Sky Bet Championship |
| 36 | Sun 5 Jul 2020 | 141-2 v Swansea CitySwansea City 2-1 Sheffield Wednesday | Sky Bet Championship |
| 37 | Wed 8 Jul 2020 | 141-3 v Preston North EndSheffield Wednesday 1-3 Preston North End | Sky Bet Championship |
| 38 | Sat 11 Jul 2020 | 143-0 v Queens Park RangersQueens Park Rangers 0-3 Sheffield Wednesday | Sky Bet Championship |
| 39 | Tue 14 Jul 2020 | 140-0 v Huddersfield TownSheffield Wednesday 0-0 Huddersfield Town | Sky Bet Championship |
| 40 | Sat 18 Jul 2020 | 143-5 v FulhamFulham 5-3 Sheffield Wednesday | Sky Bet Championship |
| 41 | Wed 22 Jul 2020 | 141-2 v MiddlesbroughSheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
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