| 1 | Tue 24 Jul 2018 | 72-3 v RochdaleRochdale 3-2 Middlesbrough | Friendly |
| 2 | Sat 4 Aug 2018 | 72-2 v MillwallMillwall 2-2 Middlesbrough | Sky Bet Championship |
| 3 | Tue 7 Aug 2018 | 73-0 v Sheffield UnitedMiddlesbrough 3-0 Sheffield United | Sky Bet Championship |
| 4 | Tue 14 Aug 2018 | 7 3-3 v Notts CountyMiddlesbrough 3-3 Notts County | Carabao Cup First Round |
| 5 | Tue 28 Aug 2018 | 72-1 v RochdaleMiddlesbrough 2-1 Rochdale | Carabao Cup Second Round |
| 6 | Tue 25 Sep 2018 | 72-2 v Preston North EndPreston North End 2-2 Middlesbrough | Carabao Cup Third Round |
| 7 | Wed 31 Oct 2018 | 71-0 v Crystal PalaceMiddlesbrough 1-0 Crystal Palace | Carabao Cup Fourth Round |
| 8 | Tue 18 Dec 2018 | 70-1 v Burton AlbionMiddlesbrough 0-1 Burton Albion | Carabao Cup Quarter Final |
| 9 | Sat 5 Jan 2019 | 7 5-0 v Peterborough UnitedMiddlesbrough 5-0 Peterborough United | Emirates FA Cup Third Round |
| 10 | Sat 2 Feb 2019 | 1-0 v AFC WimbledonSunderland 1-0 AFC Wimbledon | Sky Bet League One |
| 11 | Sat 9 Feb 2019 | 1-1 v Oxford UnitedOxford United 1-1 Sunderland | Sky Bet League One |
| 12 | Tue 12 Feb 2019 | 231-1 v BlackpoolSunderland 1-1 Blackpool | Sky Bet League One |
| 13 | Fri 15 Feb 2019 | 232-2 v Accrington StanleySunderland 2-2 Accrington Stanley | Sky Bet League One |
| 14 | Tue 19 Feb 2019 | 234-2 v GillinghamSunderland 4-2 Gillingham | Sky Bet League One |
| 15 | Sat 23 Feb 2019 | 232-0 v Bristol RoversBristol Rovers 0-2 Sunderland | Sky Bet League One |
| 16 | Sat 2 Mar 2019 | 232-0 v Plymouth ArgyleSunderland 2-0 Plymouth Argyle | Sky Bet League One |
| 17 | Tue 5 Mar 2019 | 232-0 v Bristol RoversBristol Rovers 0-2 Sunderland | Checkatrade Trophy Semi Final |
| 18 | Sat 9 Mar 2019 | 231-1 v Wycombe WanderersWycombe Wanderers 1-1 Sunderland | Sky Bet League One |
| 19 | Tue 12 Mar 2019 | 23 0-0 v BarnsleyBarnsley 0-0 Sunderland | Sky Bet League One |
| 20 | Sat 16 Mar 2019 | 23 2-1 v WalsallSunderland 2-1 Walsall | Sky Bet League One |
| 21 | Sun 31 Mar 2019 | 232-2 v PortsmouthPortsmouth 2-2 Sunderland | Checkatrade Trophy Final |
| 22 | Tue 9 Apr 2019 | 231-1 v Burton AlbionSunderland 1-1 Burton Albion | Sky Bet League One |
| 23 | Sat 13 Apr 2019 | 23 4-5 v Coventry CitySunderland 4-5 Coventry City | Sky Bet League One |
| 24 | Fri 19 Apr 2019 | 232-0 v Doncaster RoversSunderland 2-0 Doncaster Rovers | Sky Bet League One |
| 25 | Sat 4 May 2019 | 231-2 v Southend UnitedSouthend United 2-1 Sunderland | Sky Bet League One |
| 26 | Thu 16 May 2019 | 230-0 v PortsmouthPortsmouth 0-0 Sunderland | Sky Bet League One Play-off Semi Final |
| 27 | Sun 26 May 2019 | 23 1-2 v Charlton AthleticCharlton Athletic 2-1 Sunderland | Sky Bet League One Play-off Final |
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