| 1 | Sun 25 Aug 2019 | 1-3 v CelticCeltic 3-1 Heart of Midlothian | Ladbrokes Premiership |
| 2 | Sat 31 Aug 2019 | 2-2 v Hamilton AcademicalHeart of Midlothian 2-2 Hamilton Academical | Ladbrokes Premiership |
| 3 | Sat 14 Sep 2019 | 2-3 v MotherwellHeart of Midlothian 2-3 Motherwell | Ladbrokes Premiership |
| 4 | Sun 22 Sep 2019 | 2-1 v HibernianHibernian 1-2 Heart of Midlothian | Ladbrokes Premiership |
| 5 | Wed 25 Sep 2019 | 2-2 v AberdeenHeart of Midlothian 2-2 Aberdeen | Betfred Cup Quarter Final |
| 6 | Sat 28 Sep 2019 | 0-0 v St MirrenSt Mirren 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 7 | Sat 5 Oct 2019 | 0-1 v KilmarnockHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 8 | Sun 20 Oct 2019 | 1-1 v RangersHeart of Midlothian 1-1 Rangers | Ladbrokes Premiership |
| 9 | Sun 3 Nov 2019 | 0-3 v RangersRangers 3-0 Heart of Midlothian | Betfred Cup Semi Final |
| 10 | Sat 23 Nov 2019 | 0-3 v KilmarnockKilmarnock 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 11 | Sun 1 Dec 2019 | 0-5 v RangersRangers 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 12 | Wed 4 Dec 2019 | 1-1 v LivingstonHeart of Midlothian 1-1 Livingston | Ladbrokes Premiership |
| 13 | Sat 7 Dec 2019 | 0-1 v MotherwellMotherwell 1-0 Heart of Midlothian | Ladbrokes Premiership |
| 14 | Sat 14 Dec 2019 | 0-1 v St JohnstoneHeart of Midlothian 0-1 St Johnstone | Ladbrokes Premiership |
| 15 | Sat 21 Dec 2019 | 1-2 v Hamilton AcademicalHamilton Academical 2-1 Heart of Midlothian | Ladbrokes Premiership |
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