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