| 1 | Fri 2 Aug 2019 | 163-3 v Luton TownLuton Town 3-3 Middlesbrough | Sky Bet Championship |
| 2 | Sat 10 Aug 2019 | 160-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 3 | Sat 17 Aug 2019 | 160-1 v Blackburn RoversBlackburn Rovers 1-0 Middlesbrough | Sky Bet Championship |
| 4 | Tue 20 Aug 2019 | 161-0 v Wigan AthleticMiddlesbrough 1-0 Wigan Athletic | Sky Bet Championship |
| 5 | Sat 24 Aug 2019 | 161-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 6 | Tue 1 Oct 2019 | 161-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 7 | Fri 4 Oct 2019 | 161-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 8 | Sat 19 Oct 2019 | 16 0-1 v West Bromwich AlbionMiddlesbrough 0-1 West Bromwich Albion | Sky Bet Championship |
| 9 | Wed 23 Oct 2019 | 160-0 v Huddersfield TownHuddersfield Town 0-0 Middlesbrough | Sky Bet Championship |
| 10 | Sat 26 Oct 2019 | 160-0 v FulhamMiddlesbrough 0-0 Fulham | Sky Bet Championship |
| 11 | Sat 2 Nov 2019 | 160-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
| 12 | Sat 9 Nov 2019 | 162-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 13 | Sun 24 Nov 2019 | 162-2 v Hull CityMiddlesbrough 2-2 Hull City | Sky Bet Championship |
| 14 | Wed 27 Nov 2019 | 16 1-0 v BarnsleyMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
| 15 | Sat 30 Nov 2019 | 16 0-4 v Leeds UnitedLeeds United 4-0 Middlesbrough | Sky Bet Championship |
| 16 | Sat 7 Dec 2019 | 161-0 v Charlton AthleticMiddlesbrough 1-0 Charlton Athletic | Sky Bet Championship |
| 17 | Tue 10 Dec 2019 | 161-1 v Nottingham ForestNottingham Forest 1-1 Middlesbrough | Sky Bet Championship |
| 18 | Sat 14 Dec 2019 | 161-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 19 | Thu 26 Dec 2019 | 16 1-0 v Huddersfield TownMiddlesbrough 1-0 Huddersfield Town | Sky Bet Championship |
| 20 | Sun 29 Dec 2019 | 16 2-0 v West Bromwich AlbionWest Bromwich Albion 0-2 Middlesbrough | Sky Bet Championship |
| 21 | Wed 1 Jan 2020 | 162-0 v Preston North EndPreston North End 0-2 Middlesbrough | Sky Bet Championship |
| 22 | Sun 5 Jan 2020 | 161-1 v Tottenham HotspurMiddlesbrough 1-1 Tottenham Hotspur | Emirates FA Cup Third Round |
| 23 | Sat 11 Jan 2020 | 162-2 v Derby CountyMiddlesbrough 2-2 Derby County | Sky Bet Championship |
| 24 | Tue 14 Jan 2020 | 161-2 v Tottenham HotspurTottenham Hotspur 2-1 Middlesbrough | Emirates FA Cup Third Round Replay |
| 25 | Fri 17 Jan 2020 | 160-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
| 26 | Tue 21 Jan 2020 | 161-1 v Birmingham CityMiddlesbrough 1-1 Birmingham City | Sky Bet Championship |
| 27 | Sat 1 Feb 2020 | 161-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 28 | Sat 8 Feb 2020 | 162-3 v BrentfordBrentford 3-2 Middlesbrough | Sky Bet Championship |
| 29 | Tue 11 Feb 2020 | 16 2-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
| 30 | Sat 15 Feb 2020 | 160-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
| 31 | Sat 22 Feb 2020 | 160-1 v BarnsleyBarnsley 1-0 Middlesbrough | Sky Bet Championship |
| 32 | Wed 26 Feb 2020 | 160-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 33 | Mon 2 Mar 2020 | 162-2 v Nottingham ForestMiddlesbrough 2-2 Nottingham Forest | Sky Bet Championship |
| 34 | Sat 7 Mar 2020 | 161-0 v Charlton AthleticCharlton Athletic 0-1 Middlesbrough | Sky Bet Championship |
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