| 1 | Sun 4 Aug 2019 | 2-3 v AberdeenAberdeen 3-2 Heart of Midlothian | Ladbrokes Premiership |
| 2 | Sat 10 Aug 2019 | 0-0 v Ross CountyHeart of Midlothian 0-0 Ross County | Ladbrokes Premiership |
| 3 | Fri 16 Aug 2019 | 2-1 v MotherwellMotherwell 1-2 Heart of Midlothian | Betfred Cup Second Round |
| 4 | Sat 9 Nov 2019 | 5-2 v St MirrenHeart of Midlothian 5-2 St Mirren | Ladbrokes Premiership |
| 5 | Sat 23 Nov 2019 | 0-3 v KilmarnockKilmarnock 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 6 | Sun 1 Dec 2019 | 0-5 v RangersRangers 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 7 | Wed 4 Dec 2019 | 1-1 v LivingstonHeart of Midlothian 1-1 Livingston | Ladbrokes Premiership |
| 8 | Sat 7 Dec 2019 | 0-1 v MotherwellMotherwell 1-0 Heart of Midlothian | Ladbrokes Premiership |
| 9 | Sat 14 Dec 2019 | 0-1 v St JohnstoneHeart of Midlothian 0-1 St Johnstone | Ladbrokes Premiership |
| 10 | Wed 22 Jan 2020 | 0-0 v Ross CountyRoss County 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 11 | Wed 5 Feb 2020 | 2-3 v KilmarnockHeart of Midlothian 2-3 Kilmarnock | Ladbrokes Premiership |
| 12 | Wed 12 Feb 2020 | 0-5 v CelticCeltic 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 13 | Sat 15 Feb 2020 | 2-2 v Hamilton AcademicalHeart of Midlothian 2-2 Hamilton Academical | Ladbrokes Premiership |
| 14 | Tue 3 Mar 2020 | 3-1 v HibernianHibernian 1-3 Heart of Midlothian | Ladbrokes Premiership |
| 15 | Sat 7 Mar 2020 | 1-1 v MotherwellHeart of Midlothian 1-1 Motherwell | Ladbrokes Premiership |
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