| 1 | 21/7/2018 | 24-2 v DumbartonDumbarton 2-4 Kilmarnock | Betfred Cup Group H |
| 2 | 24/7/2018 | 23-0 v SpartansSpartans 0-3 Kilmarnock | Betfred Cup Group H |
| 3 | 28/7/2018 | 22-0 v Queens ParkKilmarnock 2-0 Queens Park | Betfred Cup Group H |
| 4 | 4/8/2018 | 22-0 v St JohnstoneKilmarnock 2-0 St Johnstone | Ladbrokes Premiership |
| 5 | 11/8/2018 | 20-0 v LivingstonLivingston 0-0 Kilmarnock | Ladbrokes Premiership |
| 6 | 19/8/2018 | 21-3 v RangersKilmarnock 1-3 Rangers | Betfred Cup Second Round |
| 7 | 25/8/2018 | 20-1 v Heart of MidlothianKilmarnock 0-1 Heart of Midlothian | Ladbrokes Premiership |
| 8 | 1/9/2018 | 22-0 v AberdeenAberdeen 0-2 Kilmarnock | Ladbrokes Premiership |
| 9 | 10/9/2018 | 2-0 v AlbaniaScotland 2-0 Albania | UEFA Nations League League C Group 1 |
| 10 | 15/9/2018 | 22-3 v HibernianHibernian 3-2 Kilmarnock | Ladbrokes Premiership |
| 11 | 23/9/2018 | 22-1 v CelticKilmarnock 2-1 Celtic | Ladbrokes Premiership |
| 12 | 29/9/2018 | 23-1 v MotherwellKilmarnock 3-1 Motherwell | Ladbrokes Premiership |
| 13 | 6/10/2018 | 22-1 v DundeeDundee 1-2 Kilmarnock | Ladbrokes Premiership |
| 14 | 11/10/2018 | 1-2 v IsraelIsrael 2-1 Scotland | UEFA Nations League League C Group 1 |
| 15 | 14/10/2018 | 1-3 v PortugalScotland 1-3 Portugal | International Friendly |
| 16 | 20/10/2018 | 2 2-1 v St MirrenSt Mirren 1-2 Kilmarnock | Ladbrokes Premiership |
| 17 | 27/10/2018 | 21-1 v Hamilton AcademicalKilmarnock 1-1 Hamilton Academical | Ladbrokes Premiership |
| 18 | 31/10/2018 | 2 1-1 v RangersRangers 1-1 Kilmarnock | Ladbrokes Premiership |
| 19 | 4/11/2018 | 21-2 v AberdeenKilmarnock 1-2 Aberdeen | Ladbrokes Premiership |
| 20 | 24/11/2018 | 20-0 v St JohnstoneSt Johnstone 0-0 Kilmarnock | Ladbrokes Premiership |
| 21 | 1/12/2018 | 23-0 v HibernianKilmarnock 3-0 Hibernian | Ladbrokes Premiership |
| 22 | 5/12/2018 | 22-0 v LivingstonKilmarnock 2-0 Livingston | Ladbrokes Premiership |
| 23 | 8/12/2018 | 2 1-5 v CelticCeltic 5-1 Kilmarnock | Ladbrokes Premiership |
| 24 | 15/12/2018 | 23-1 v DundeeKilmarnock 3-1 Dundee | Ladbrokes Premiership |
| 25 | 22/12/2018 | 21-1 v Hamilton AcademicalHamilton Academical 1-1 Kilmarnock | Ladbrokes Premiership |
| 26 | 26/12/2018 | 21-0 v MotherwellMotherwell 0-1 Kilmarnock | Ladbrokes Premiership |
| 27 | 29/12/2018 | 22-1 v St MirrenKilmarnock 2-1 St Mirren | Ladbrokes Premiership |
| 28 | 19/1/2019 | 22-0 v Forfar AthleticKilmarnock 2-0 Forfar Athletic | William Hill Scottish Cup Fourth Round |
| 29 | 23/1/2019 | 22-1 v RangersKilmarnock 2-1 Rangers | Ladbrokes Premiership |
| 30 | 26/1/2019 | 20-0 v AberdeenAberdeen 0-0 Kilmarnock | Ladbrokes Premiership |
| 31 | 1/2/2019 | 21-2 v Heart of MidlothianKilmarnock 1-2 Heart of Midlothian | Ladbrokes Premiership |
| 32 | 6/2/2019 | 22-2 v DundeeDundee 2-2 Kilmarnock | Ladbrokes Premiership |
| 33 | 17/2/2019 | 20-1 v CelticKilmarnock 0-1 Celtic | Ladbrokes Premiership |