| 1 | Sat 14 Sep 2019 | 182-3 v MotherwellHeart of Midlothian 2-3 Motherwell | Ladbrokes Premiership |
| 2 | Wed 25 Sep 2019 | 182-2 v AberdeenHeart of Midlothian 2-2 Aberdeen | Betfred Cup Quarter Final |
| 3 | Sat 28 Sep 2019 | 180-0 v St MirrenSt Mirren 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 4 | Sat 5 Oct 2019 | 180-1 v KilmarnockHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 5 | Sun 20 Oct 2019 | 18 1-1 v RangersHeart of Midlothian 1-1 Rangers | Ladbrokes Premiership |
| 6 | Sat 26 Oct 2019 | 180-0 v LivingstonLivingston 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 7 | Sun 3 Nov 2019 | 18 0-3 v RangersRangers 3-0 Heart of Midlothian | Betfred Cup Semi Final |
| 8 | Wed 4 Dec 2019 | 181-1 v LivingstonHeart of Midlothian 1-1 Livingston | Ladbrokes Premiership |
| 9 | Sat 7 Dec 2019 | 180-1 v MotherwellMotherwell 1-0 Heart of Midlothian | Ladbrokes Premiership |
| 10 | Sat 14 Dec 2019 | 180-1 v St JohnstoneHeart of Midlothian 0-1 St Johnstone | Ladbrokes Premiership |
| 11 | Sat 21 Dec 2019 | 18 1-2 v Hamilton AcademicalHamilton Academical 2-1 Heart of Midlothian | Ladbrokes Premiership |
| 12 | Sat 8 Feb 2020 | 1-1 v StranraerStranraer 1-1 Raith Rovers | Ladbrokes League One |
| 13 | Fri 14 Feb 2020 | 2-1 v Partick ThistlePartick Thistle 1-2 Raith Rovers | Tunnock's Challenge Cup Semi Final |
| 14 | Sat 22 Feb 2020 | 1-0 v ClydeRaith Rovers 1-0 Clyde | Ladbrokes League One |
| 15 | Sat 29 Feb 2020 | 0-1 v DumbartonDumbarton 1-0 Raith Rovers | Ladbrokes League One |
| 16 | Tue 3 Mar 2020 | 1-1 v FalkirkRaith Rovers 1-1 Falkirk | Ladbrokes League One |
| 17 | Sat 7 Mar 2020 | 2-1 v Forfar AthleticRaith Rovers 2-1 Forfar Athletic | Ladbrokes League One |
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