| 1 | Sat 25 Aug 2018 | 1-0 v KilmarnockKilmarnock 0-1 Heart of Midlothian | Ladbrokes Premiership |
| 2 | Sat 1 Sep 2018 | 34-1 v St MirrenHeart of Midlothian 4-1 St Mirren | Ladbrokes Premiership |
| 3 | Sat 15 Sep 2018 | 31-0 v MotherwellMotherwell 0-1 Heart of Midlothian | Ladbrokes Premiership |
| 4 | Sat 22 Sep 2018 | 30-0 v LivingstonHeart of Midlothian 0-0 Livingston | Ladbrokes Premiership |
| 5 | Wed 26 Sep 2018 | 34-2 v MotherwellHeart of Midlothian 4-2 Motherwell | Betfred Cup Quarter Final |
| 6 | Sat 29 Sep 2018 | 32-1 v St JohnstoneHeart of Midlothian 2-1 St Johnstone | Ladbrokes Premiership |
| 7 | Sun 7 Oct 2018 | 3 1-3 v RangersRangers 3-1 Heart of Midlothian | Ladbrokes Premiership |
| 8 | Sat 20 Oct 2018 | 32-1 v AberdeenHeart of Midlothian 2-1 Aberdeen | Ladbrokes Premiership |
| 9 | Tue 23 Oct 2018 | 33-0 v DundeeDundee 0-3 Heart of Midlothian | Ladbrokes Premiership |
| 10 | Sun 28 Oct 2018 | 30-3 v CelticHeart of Midlothian 0-3 Celtic | Betfred Cup Semi Final |
| 11 | Wed 31 Oct 2018 | 30-0 v HibernianHeart of Midlothian 0-0 Hibernian | Ladbrokes Premiership |
| 12 | Sat 3 Nov 2018 | 30-5 v CelticCeltic 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 13 | Sat 10 Nov 2018 | 30-1 v KilmarnockHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 14 | Sat 24 Nov 2018 | 30-2 v St MirrenSt Mirren 2-0 Heart of Midlothian | Ladbrokes Premiership |
| 15 | Sat 19 Jan 2019 | 1-1 v Scunthorpe UnitedScunthorpe United 1-1 Sunderland | Sky Bet League One |
| 16 | Sat 2 Feb 2019 | 1-0 v AFC WimbledonSunderland 1-0 AFC Wimbledon | Sky Bet League One |
| 17 | Sat 9 Feb 2019 | 1-1 v Oxford UnitedOxford United 1-1 Sunderland | Sky Bet League One |
| 18 | Tue 12 Feb 2019 | 1-1 v BlackpoolSunderland 1-1 Blackpool | Sky Bet League One |
| 19 | Fri 15 Feb 2019 | 2-2 v Accrington StanleySunderland 2-2 Accrington Stanley | Sky Bet League One |
| 20 | Tue 19 Feb 2019 | 4-2 v GillinghamSunderland 4-2 Gillingham | Sky Bet League One |
| 21 | Sat 23 Feb 2019 | 2-0 v Bristol RoversBristol Rovers 0-2 Sunderland | Sky Bet League One |
| 22 | Sat 2 Mar 2019 | 2-0 v Plymouth ArgyleSunderland 2-0 Plymouth Argyle | Sky Bet League One |
| 23 | Tue 5 Mar 2019 | 2-0 v Bristol RoversBristol Rovers 0-2 Sunderland | Checkatrade Trophy Semi Final |
| 24 | Sat 9 Mar 2019 | 1-1 v Wycombe WanderersWycombe Wanderers 1-1 Sunderland | Sky Bet League One |
| 25 | Tue 12 Mar 2019 | 0-0 v BarnsleyBarnsley 0-0 Sunderland | Sky Bet League One |
| 26 | Wed 3 Apr 2019 | 3-0 v Accrington StanleyAccrington Stanley 0-3 Sunderland | Sky Bet League One |
| 27 | Fri 19 Apr 2019 | 2-0 v Doncaster RoversSunderland 2-0 Doncaster Rovers | Sky Bet League One |
| 28 | Mon 22 Apr 2019 | 1-1 v Peterborough UnitedPeterborough United 1-1 Sunderland | Sky Bet League One |
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