| 1 | Sun 4 Aug 2019 | 1-2 v RangersKilmarnock 1-2 Rangers | Ladbrokes Premiership |
| 2 | Sat 10 Aug 2019 | 0-2 v Hamilton AcademicalHamilton Academical 2-0 Kilmarnock | Ladbrokes Premiership |
| 3 | Sat 17 Aug 2019 | 1-0 v Hamilton AcademicalKilmarnock 1-0 Hamilton Academical | Betfred Cup Second Round |
| 4 | Sat 24 Aug 2019 | 0-0 v AberdeenKilmarnock 0-0 Aberdeen | Ladbrokes Premiership |
| 5 | Sat 31 Aug 2019 | 1-0 v St JohnstoneSt Johnstone 0-1 Kilmarnock | Ladbrokes Premiership |
| 6 | Sat 14 Sep 2019 | 2-0 v HibernianKilmarnock 2-0 Hibernian | Ladbrokes Premiership |
| 7 | Sun 22 Sep 2019 | 1-3 v CelticCeltic 3-1 Kilmarnock | Ladbrokes Premiership |
| 8 | Wed 25 Sep 2019 | 0-0 v HibernianKilmarnock 0-0 Hibernian | Betfred Cup Quarter Final |
| 9 | Sat 28 Sep 2019 | 0-0 v Ross CountyKilmarnock 0-0 Ross County | Ladbrokes Premiership |
| 10 | Sat 5 Oct 2019 | 1-0 v Heart of MidlothianHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 11 | Sat 19 Oct 2019 | 2-1 v LivingstonKilmarnock 2-1 Livingston | Ladbrokes Premiership |
| 12 | Sat 26 Oct 2019 | 1-0 v St MirrenKilmarnock 1-0 St Mirren | Ladbrokes Premiership |
| 13 | Sat 2 Nov 2019 | 0-3 v AberdeenAberdeen 3-0 Kilmarnock | Ladbrokes Premiership |
| 14 | Sat 9 Nov 2019 | 2-2 v Hamilton AcademicalKilmarnock 2-2 Hamilton Academical | Ladbrokes Premiership |
| 15 | Sat 23 Nov 2019 | 3-0 v Heart of MidlothianKilmarnock 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 16 | Sat 30 Nov 2019 | 2-2 v HibernianHibernian 2-2 Kilmarnock | Ladbrokes Premiership |
| 17 | Wed 4 Dec 2019 | 0-0 v St JohnstoneKilmarnock 0-0 St Johnstone | Ladbrokes Premiership |
| 18 | Sat 7 Dec 2019 | 0-3 v LivingstonLivingston 3-0 Kilmarnock | Ladbrokes Premiership |
| 19 | Sat 14 Dec 2019 | 0-1 v Ross CountyRoss County 1-0 Kilmarnock | Ladbrokes Premiership |
| 20 | Sat 21 Dec 2019 | 0-1 v MotherwellKilmarnock 0-1 Motherwell | Ladbrokes Premiership |
| 21 | Thu 26 Dec 2019 | 0-1 v RangersRangers 1-0 Kilmarnock | Ladbrokes Premiership |
| 22 | Sun 29 Dec 2019 | 0-1 v St MirrenSt Mirren 1-0 Kilmarnock | Ladbrokes Premiership |
| 23 | Sat 1 Feb 2020 | 3-1 v Ross CountyKilmarnock 3-1 Ross County | Ladbrokes Premiership |
| 24 | Wed 5 Feb 2020 | 3-2 v Heart of MidlothianHeart of Midlothian 2-3 Kilmarnock | Ladbrokes Premiership |
| 25 | Sat 8 Feb 2020 | 0-0 v AberdeenAberdeen 0-0 Kilmarnock | William Hill Scottish Cup Fifth Round |
| 26 | Wed 19 Feb 2020 | 3-4 v AberdeenKilmarnock 3-4 Aberdeen | William Hill Scottish Cup Fifth Round Replay |
| 27 | Sun 23 Feb 2020 | 1-3 v CelticCeltic 3-1 Kilmarnock | Ladbrokes Premiership |
| 28 | Wed 4 Mar 2020 | 2-2 v AberdeenKilmarnock 2-2 Aberdeen | Ladbrokes Premiership |
| 29 | Sat 7 Mar 2020 | 0-1 v Hamilton AcademicalHamilton Academical 1-0 Kilmarnock | Ladbrokes Premiership |
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