| 1 | Tue 26 Mar 2019 | 61-0 v GeorgiaRepublic of Ireland 1-0 Georgia | European Championship Qualification Group D |
| 2 | Fri 7 Jun 2019 | 1-1 v DenmarkDenmark 1-1 Republic of Ireland | European Championship Qualification Group D |
| 3 | Sun 25 Aug 2019 | 1-3 v CelticCeltic 3-1 Heart of Midlothian | Ladbrokes Premiership |
| 4 | Sat 31 Aug 2019 | 2-2 v Hamilton AcademicalHeart of Midlothian 2-2 Hamilton Academical | Ladbrokes Premiership |
| 5 | Thu 5 Sep 2019 | 1-1 v SwitzerlandRepublic of Ireland 1-1 Switzerland | European Championship Qualification Group D |
| 6 | Sat 14 Sep 2019 | 2-3 v MotherwellHeart of Midlothian 2-3 Motherwell | Ladbrokes Premiership |
| 7 | Sun 22 Sep 2019 | 2-1 v HibernianHibernian 1-2 Heart of Midlothian | Ladbrokes Premiership |
| 8 | Wed 25 Sep 2019 | 2-2 v AberdeenHeart of Midlothian 2-2 Aberdeen | Betfred Cup Quarter Final |
| 9 | Sat 28 Sep 2019 | 0-0 v St MirrenSt Mirren 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 10 | Sat 5 Oct 2019 | 0-1 v KilmarnockHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 11 | Sat 12 Oct 2019 | 0-0 v GeorgiaGeorgia 0-0 Republic of Ireland | European Championship Qualification Group D |
| 12 | Tue 15 Oct 2019 | 0-2 v SwitzerlandSwitzerland 2-0 Republic of Ireland | European Championship Qualification Group D |
| 13 | Sun 20 Oct 2019 | 1-1 v RangersHeart of Midlothian 1-1 Rangers | Ladbrokes Premiership |
| 14 | Sun 3 Nov 2019 | 0-3 v RangersRangers 3-0 Heart of Midlothian | Betfred Cup Semi Final |
| 15 | Mon 18 Nov 2019 | 1-1 v DenmarkRepublic of Ireland 1-1 Denmark | European Championship Qualification Group D |
| 16 | Sat 23 Nov 2019 | 0-3 v KilmarnockKilmarnock 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 17 | Sun 1 Dec 2019 | 0-5 v RangersRangers 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 18 | Wed 4 Dec 2019 | 1-1 v LivingstonHeart of Midlothian 1-1 Livingston | Ladbrokes Premiership |
| 19 | Sat 7 Dec 2019 | 0-1 v MotherwellMotherwell 1-0 Heart of Midlothian | Ladbrokes Premiership |
| 20 | Sat 14 Dec 2019 | 0-1 v St JohnstoneHeart of Midlothian 0-1 St Johnstone | Ladbrokes Premiership |
| 21 | Sat 21 Dec 2019 | 1-2 v Hamilton AcademicalHamilton Academical 2-1 Heart of Midlothian | Ladbrokes Premiership |
| 22 | Sat 1 Feb 2020 | 2-1 v Doncaster RoversFleetwood Town 2-1 Doncaster Rovers | Sky Bet League One |
| 23 | Sat 8 Feb 2020 | 2-1 v AFC WimbledonAFC Wimbledon 1-2 Fleetwood Town | Sky Bet League One |
| 24 | Tue 11 Feb 2020 | 1-0 v Wycombe WanderersWycombe Wanderers 0-1 Fleetwood Town | Sky Bet League One |
| 25 | Sat 15 Feb 2020 | 2-1 v Peterborough UnitedFleetwood Town 2-1 Peterborough United | Sky Bet League One |
| 26 | Sat 22 Feb 2020 | 1-0 v PortsmouthFleetwood Town 1-0 Portsmouth | Sky Bet League One |
| 27 | Tue 25 Feb 2020 | 1-1 v SunderlandSunderland 1-1 Fleetwood Town | Sky Bet League One |
| 28 | Tue 3 Mar 2020 | 1-0 v Ipswich TownIpswich Town 0-1 Fleetwood Town | Sky Bet League One |
| 29 | Sat 7 Mar 2020 | 0-0 v BlackpoolFleetwood Town 0-0 Blackpool | Sky Bet League One |
| 30 | Tue 10 Mar 2020 | 2-2 v PortsmouthPortsmouth 2-2 Fleetwood Town | Sky Bet League One |
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