| 1 | Sat 3 Aug 2019 | 1-0 v St MirrenHibernian 1-0 St Mirren | Ladbrokes Premiership |
| 2 | Sun 11 Aug 2019 | 1-6 v RangersRangers 6-1 Hibernian | Ladbrokes Premiership |
| 3 | Sat 24 Aug 2019 | 2-2 v St JohnstoneHibernian 2-2 St Johnstone | Ladbrokes Premiership |
| 4 | Sat 31 Aug 2019 | 0-3 v MotherwellMotherwell 3-0 Hibernian | Ladbrokes Premiership |
| 5 | Sat 14 Sep 2019 | 0-2 v KilmarnockKilmarnock 2-0 Hibernian | Ladbrokes Premiership |
| 6 | Sun 22 Sep 2019 | 1-2 v Heart of MidlothianHibernian 1-2 Heart of Midlothian | Ladbrokes Premiership |
| 7 | Sat 5 Oct 2019 | 1-1 v AberdeenAberdeen 1-1 Hibernian | Ladbrokes Premiership |
| 8 | Sat 19 Oct 2019 | 1-1 v Hamilton AcademicalHamilton Academical 1-1 Hibernian | Ladbrokes Premiership |
| 9 | Sat 26 Oct 2019 | 2-2 v Ross CountyHibernian 2-2 Ross County | Ladbrokes Premiership |
| 10 | Sat 2 Nov 2019 | 2-5 v CelticHibernian 2-5 Celtic | Betfred Cup Semi Final |
| 11 | Sat 9 Nov 2019 | 4-1 v St JohnstoneSt Johnstone 1-4 Hibernian | Ladbrokes Premiership |
| 12 | Sat 23 Nov 2019 | 3-1 v MotherwellHibernian 3-1 Motherwell | Ladbrokes Premiership |
| 13 | Sat 30 Nov 2019 | 2-2 v KilmarnockHibernian 2-2 Kilmarnock | Ladbrokes Premiership |
| 14 | Wed 4 Dec 2019 | 1-2 v Ross CountyRoss County 2-1 Hibernian | Ladbrokes Premiership |
| 15 | Sat 7 Dec 2019 | 3-0 v AberdeenHibernian 3-0 Aberdeen | Ladbrokes Premiership |
| 16 | Sun 15 Dec 2019 | 0-2 v CelticCeltic 2-0 Hibernian | Ladbrokes Premiership |
| 17 | Fri 20 Dec 2019 | 0-3 v RangersHibernian 0-3 Rangers | Ladbrokes Premiership |
| 18 | Sun 19 Jan 2020 | 2-2 v Dundee UnitedDundee United 2-2 Hibernian | William Hill Scottish Cup Fourth Round |
| 19 | Wed 22 Jan 2020 | 2-1 v Hamilton AcademicalHibernian 2-1 Hamilton Academical | Ladbrokes Premiership |
| 20 | Sat 25 Jan 2020 | 0-0 v MotherwellMotherwell 0-0 Hibernian | Ladbrokes Premiership |
| 21 | Sat 1 Feb 2020 | 0-0 v AberdeenRangers 0-0 Aberdeen | Ladbrokes Premiership |
| 22 | Wed 12 Feb 2020 | 1-2 v KilmarnockKilmarnock 2-1 Rangers | Ladbrokes Premiership |
| 23 | Sun 16 Feb 2020 | 1-0 v LivingstonRangers 1-0 Livingston | Ladbrokes Premiership |
| 24 | Thu 20 Feb 2020 | 3-2 v Sporting BragaRangers 3-2 Sporting Braga | Europa League Round of 32 |
| 25 | Sun 23 Feb 2020 | 2-2 v St JohnstoneSt Johnstone 2-2 Rangers | Ladbrokes Premiership |
| 26 | Wed 26 Feb 2020 | 1-0 v Sporting BragaSporting Braga 0-1 Rangers | Europa League Round of 32 |
| 27 | Wed 4 Mar 2020 | 0-1 v Hamilton AcademicalRangers 0-1 Hamilton Academical | Ladbrokes Premiership |
| 28 | Sun 8 Mar 2020 | 1-0 v Ross CountyRoss County 0-1 Rangers | Ladbrokes Premiership |
| 29 | Thu 12 Mar 2020 | 1-3 v Bayer 04 LeverkusenRangers 1-3 Bayer 04 Leverkusen | Europa League Round of 16 |
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