| 1 | 18/7/2018 | 12-1 v Cove RangersCove Rangers 1-2 Heart of Midlothian | Betfred Cup Group C |
| 2 | 21/7/2018 | 11-1 v Raith RoversRaith Rovers 1-1 Heart of Midlothian | Betfred Cup Group C |
| 3 | 24/7/2018 | 15-0 v CowdenbeathHeart of Midlothian 5-0 Cowdenbeath | Betfred Cup Group C |
| 4 | 29/7/2018 | 15-0 v Inverness Caledonian ThistleHeart of Midlothian 5-0 Inverness Caledonian Thistle | Betfred Cup Group C |
| 5 | 4/8/2018 | 14-1 v Hamilton AcademicalHamilton Academical 1-4 Heart of Midlothian | Ladbrokes Premiership |
| 6 | 11/8/2018 | 11-0 v CelticHeart of Midlothian 1-0 Celtic | Ladbrokes Premiership |
| 7 | 18/8/2018 | 11-0 v Dunfermline AthleticDunfermline Athletic 0-1 Heart of Midlothian | Betfred Cup Second Round |
| 8 | 25/8/2018 | 1 1-0 v KilmarnockKilmarnock 0-1 Heart of Midlothian | Ladbrokes Premiership |
| 9 | 1/9/2018 | 14-1 v St MirrenHeart of Midlothian 4-1 St Mirren | Ladbrokes Premiership |
| 10 | 15/9/2018 | 11-0 v MotherwellMotherwell 0-1 Heart of Midlothian | Ladbrokes Premiership |
| 11 | 22/9/2018 | 10-0 v LivingstonHeart of Midlothian 0-0 Livingston | Ladbrokes Premiership |
| 12 | 26/9/2018 | 14-2 v MotherwellHeart of Midlothian 4-2 Motherwell | Betfred Cup Quarter Final |
| 13 | 29/9/2018 | 12-1 v St JohnstoneHeart of Midlothian 2-1 St Johnstone | Ladbrokes Premiership |
| 14 | 7/10/2018 | 11-3 v RangersRangers 3-1 Heart of Midlothian | Ladbrokes Premiership |
| 15 | 20/10/2018 | 12-1 v AberdeenHeart of Midlothian 2-1 Aberdeen | Ladbrokes Premiership |
| 16 | 23/10/2018 | 13-0 v DundeeDundee 0-3 Heart of Midlothian | Ladbrokes Premiership |
| 17 | 28/10/2018 | 10-3 v CelticHeart of Midlothian 0-3 Celtic | Betfred Cup Semi Final |
| 18 | 31/10/2018 | 10-0 v HibernianHeart of Midlothian 0-0 Hibernian | Ladbrokes Premiership |
| 19 | 3/11/2018 | 10-5 v CelticCeltic 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 20 | 10/11/2018 | 10-1 v KilmarnockHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 21 | 24/11/2018 | 10-2 v St MirrenSt Mirren 2-0 Heart of Midlothian | Ladbrokes Premiership |
| 22 | 2/12/2018 | 11-2 v RangersHeart of Midlothian 1-2 Rangers | Ladbrokes Premiership |
| 23 | 5/12/2018 | 12-2 v St JohnstoneSt Johnstone 2-2 Heart of Midlothian | Ladbrokes Premiership |
| 24 | 8/12/2018 | 11-0 v MotherwellHeart of Midlothian 1-0 Motherwell | Ladbrokes Premiership |
| 25 | 14/12/2018 | 1 0-5 v LivingstonLivingston 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 26 | 23/2/2019 | 11-1 v St MirrenHeart of Midlothian 1-1 St Mirren | Ladbrokes Premiership |
| 27 | 27/2/2019 | 11-2 v CelticHeart of Midlothian 1-2 Celtic | Ladbrokes Premiership |
| 28 | 4/3/2019 | 11-1 v Partick ThistlePartick Thistle 1-1 Heart of Midlothian | William Hill Scottish Cup Quarter Final |
| 29 | 9/3/2019 | 1 1-0 v DundeeDundee 0-1 Heart of Midlothian | Ladbrokes Premiership |
| 30 | 12/3/2019 | 12-1 v Partick ThistleHeart of Midlothian 2-1 Partick Thistle | William Hill Scottish Cup Quarter Final Replay |
| 31 | 16/3/2019 | 10-1 v Hamilton AcademicalHamilton Academical 1-0 Heart of Midlothian | Ladbrokes Premiership |
| 32 | 30/3/2019 | 12-1 v AberdeenHeart of Midlothian 2-1 Aberdeen | Ladbrokes Premiership |
| 33 | 3/4/2019 | 10-3 v RangersRangers 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 34 | 6/4/2019 | 11-2 v HibernianHeart of Midlothian 1-2 Hibernian | Ladbrokes Premiership |
| 35 | 13/4/2019 | 13-0 v Inverness Caledonian ThistleHeart of Midlothian 3-0 Inverness Caledonian Thistle | William Hill Scottish Cup Semi Final |
| 36 | 20/4/2019 | 11-3 v RangersHeart of Midlothian 1-3 Rangers | Ladbrokes Premiership |
| 37 | 28/4/2019 | 11-1 v HibernianHibernian 1-1 Heart of Midlothian | Ladbrokes Premiership |
| 38 | 4/5/2019 | 10-1 v KilmarnockHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 39 | 25/5/2019 | 1 1-2 v CelticHeart of Midlothian 1-2 Celtic | William Hill Scottish Cup Final |
