| 1 | Sat 10 Aug 2019 | 0-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 2 | Tue 13 Aug 2019 | 2-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 0-1 v Blackburn RoversBlackburn Rovers 1-0 Middlesbrough | Sky Bet Championship |
| 4 | Sat 31 Aug 2019 | 2-2 v Bristol CityBristol City 2-2 Middlesbrough | Sky Bet Championship |
| 5 | Sat 14 Sep 2019 | 1-0 v ReadingMiddlesbrough 1-0 Reading | Sky Bet Championship |
| 6 | Sat 21 Sep 2019 | 0-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 7 | Sat 28 Sep 2019 | 1-4 v Sheffield WednesdayMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 8 | Tue 1 Oct 2019 | 1-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 9 | Fri 4 Oct 2019 | 1-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 10 | Sat 2 Nov 2019 | 0-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
| 11 | Sat 9 Nov 2019 | 2-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 12 | Sun 24 Nov 2019 | 2-2 v Hull CityMiddlesbrough 2-2 Hull City | Sky Bet Championship |
| 13 | Wed 27 Nov 2019 | 1-0 v BarnsleyMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
| 14 | Wed 8 Jul 2020 | 22-0 v MillwallMillwall 0-2 Middlesbrough | Sky Bet Championship |
| 15 | Tue 14 Jul 2020 | 22-1 v ReadingReading 1-2 Middlesbrough | Sky Bet Championship |
| 16 | Sat 18 Jul 2020 | 21-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
| 17 | Wed 22 Jul 2020 | 22-1 v Sheffield WednesdaySheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
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