| 1 | Sat 24 Aug 2019 | 0-0 v AberdeenKilmarnock 0-0 Aberdeen | Ladbrokes Premiership |
| 2 | Sat 31 Aug 2019 | 1-0 v St JohnstoneSt Johnstone 0-1 Kilmarnock | Ladbrokes Premiership |
| 3 | Sat 28 Sep 2019 | 0-0 v Ross CountyKilmarnock 0-0 Ross County | Ladbrokes Premiership |
| 4 | Sat 5 Oct 2019 | 1-0 v Heart of MidlothianHeart of Midlothian 0-1 Kilmarnock | Ladbrokes Premiership |
| 5 | Sat 19 Oct 2019 | 2-1 v LivingstonKilmarnock 2-1 Livingston | Ladbrokes Premiership |
| 6 | Sat 26 Oct 2019 | 1-0 v St MirrenKilmarnock 1-0 St Mirren | Ladbrokes Premiership |
| 7 | Sat 9 Nov 2019 | 2-2 v Hamilton AcademicalKilmarnock 2-2 Hamilton Academical | Ladbrokes Premiership |
| 8 | Sat 23 Nov 2019 | 3-0 v Heart of MidlothianKilmarnock 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 9 | Sat 30 Nov 2019 | 2-2 v HibernianHibernian 2-2 Kilmarnock | Ladbrokes Premiership |
| 10 | Wed 4 Dec 2019 | 0-0 v St JohnstoneKilmarnock 0-0 St Johnstone | Ladbrokes Premiership |
| 11 | Sat 7 Dec 2019 | 0-3 v LivingstonLivingston 3-0 Kilmarnock | Ladbrokes Premiership |
| 12 | Thu 26 Dec 2019 | 0-1 v RangersRangers 1-0 Kilmarnock | Ladbrokes Premiership |
| 13 | Sun 29 Dec 2019 | 0-1 v St MirrenSt Mirren 1-0 Kilmarnock | Ladbrokes Premiership |
| 14 | Sat 18 Jan 2020 | 6-0 v Queens ParkKilmarnock 6-0 Queens Park | William Hill Scottish Cup Fourth Round |
| 15 | Wed 22 Jan 2020 | 1-3 v CelticKilmarnock 1-3 Celtic | Ladbrokes Premiership |
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