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