| 1 | Sat 3 Aug 2019 | 1 3-1 v ReadingReading 1-3 Sheffield Wednesday | Sky Bet Championship |
| 2 | Sat 17 Aug 2019 | 10-1 v MillwallMillwall 1-0 Sheffield Wednesday | Sky Bet Championship |
| 3 | Tue 20 Aug 2019 | 11-0 v Luton TownSheffield Wednesday 1-0 Luton Town | Sky Bet Championship |
| 4 | Sat 24 Aug 2019 | 11-2 v Preston North EndPreston North End 2-1 Sheffield Wednesday | Sky Bet Championship |
| 5 | Sat 31 Aug 2019 | 11-2 v Queens Park RangersSheffield Wednesday 1-2 Queens Park Rangers | Sky Bet Championship |
| 6 | Sun 15 Sep 2019 | 12-0 v Huddersfield TownHuddersfield Town 0-2 Sheffield Wednesday | Sky Bet Championship |
| 7 | Sat 21 Sep 2019 | 11-1 v FulhamSheffield Wednesday 1-1 Fulham | Sky Bet Championship |
| 8 | Sat 28 Sep 2019 | 14-1 v MiddlesbroughMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 9 | Tue 1 Oct 2019 | 10-1 v Hull CityHull City 1-0 Sheffield Wednesday | Sky Bet Championship |
| 10 | Sat 5 Oct 2019 | 11-0 v Wigan AthleticSheffield Wednesday 1-0 Wigan Athletic | Sky Bet Championship |
| 11 | Fri 18 Oct 2019 | 11-1 v Cardiff CityCardiff City 1-1 Sheffield Wednesday | Sky Bet Championship |
| 12 | Sat 26 Oct 2019 | 10-0 v Leeds UnitedSheffield Wednesday 0-0 Leeds United | Sky Bet Championship |
| 13 | Sat 2 Nov 2019 | 11-2 v Blackburn RoversBlackburn Rovers 2-1 Sheffield Wednesday | Sky Bet Championship |
| 14 | Sat 23 Nov 2019 | 11-2 v West Bromwich AlbionWest Bromwich Albion 2-1 Sheffield Wednesday | Sky Bet Championship |
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