| 1 | Sun 4 Aug 2019 | 22-3 v AberdeenAberdeen 3-2 Heart of Midlothian | Ladbrokes Premiership |
| 2 | Sat 10 Aug 2019 | 20-0 v Ross CountyHeart of Midlothian 0-0 Ross County | Ladbrokes Premiership |
| 3 | Fri 16 Aug 2019 | 22-1 v MotherwellMotherwell 1-2 Heart of Midlothian | Betfred Cup Second Round |
| 4 | Sun 25 Aug 2019 | 21-3 v CelticCeltic 3-1 Heart of Midlothian | Ladbrokes Premiership |
| 5 | Sun 22 Sep 2019 | 22-1 v HibernianHibernian 1-2 Heart of Midlothian | Ladbrokes Premiership |
| 6 | Wed 25 Sep 2019 | 22-2 v AberdeenHeart of Midlothian 2-2 Aberdeen | Betfred Cup Quarter Final |
| 7 | Sat 28 Sep 2019 | 20-0 v St MirrenSt Mirren 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 8 | Sat 5 Oct 2019 | 20-1 v KilmarnockHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 9 | Sun 20 Oct 2019 | 21-1 v RangersHeart of Midlothian 1-1 Rangers | Ladbrokes Premiership |
| 10 | Sat 26 Oct 2019 | 20-0 v LivingstonLivingston 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 11 | Sun 3 Nov 2019 | 20-3 v RangersRangers 3-0 Heart of Midlothian | Betfred Cup Semi Final |
| 12 | Sat 9 Nov 2019 | 25-2 v St MirrenHeart of Midlothian 5-2 St Mirren | Ladbrokes Premiership |
| 13 | Sat 23 Nov 2019 | 20-3 v KilmarnockKilmarnock 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 14 | Wed 4 Dec 2019 | 21-1 v LivingstonHeart of Midlothian 1-1 Livingston | Ladbrokes Premiership |
| 15 | Sat 7 Dec 2019 | 20-1 v MotherwellMotherwell 1-0 Heart of Midlothian | Ladbrokes Premiership |
| 16 | Sat 14 Dec 2019 | 2 0-1 v St JohnstoneHeart of Midlothian 0-1 St Johnstone | Ladbrokes Premiership |
| 17 | Sat 21 Dec 2019 | 2 1-2 v Hamilton AcademicalHamilton Academical 2-1 Heart of Midlothian | Ladbrokes Premiership |
| 18 | Thu 26 Dec 2019 | 2 0-2 v HibernianHeart of Midlothian 0-2 Hibernian | Ladbrokes Premiership |
| 19 | Sun 29 Dec 2019 | 21-1 v AberdeenHeart of Midlothian 1-1 Aberdeen | Ladbrokes Premiership |
| 20 | Sat 18 Jan 2020 | 25-0 v AirdrieoniansHeart of Midlothian 5-0 Airdrieonians | William Hill Scottish Cup Fourth Round |
| 21 | Sat 8 Feb 2020 | 21-0 v FalkirkFalkirk 0-1 Heart of Midlothian | William Hill Scottish Cup Fifth Round |
| 22 | Wed 12 Feb 2020 | 20-5 v CelticCeltic 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 23 | Sat 15 Feb 2020 | 2 2-2 v Hamilton AcademicalHeart of Midlothian 2-2 Hamilton Academical | Ladbrokes Premiership |
| 24 | Sat 29 Feb 2020 | 21-0 v RangersHeart of Midlothian 1-0 Rangers | William Hill Scottish Cup Quarter Final |
| 25 | Tue 3 Mar 2020 | 23-1 v HibernianHibernian 1-3 Heart of Midlothian | Ladbrokes Premiership |
| 26 | Sat 7 Mar 2020 | 21-1 v MotherwellHeart of Midlothian 1-1 Motherwell | Ladbrokes Premiership |
| 27 | Wed 11 Mar 2020 | 20-1 v St MirrenSt Mirren 1-0 Heart of Midlothian | Ladbrokes Premiership |
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