| 1 | 14/7/2018 | 14-0 v Stirling AlbionStirling Albion 0-4 Dundee | Betfred Cup Group D |
| 2 | 22/7/2018 | 10-1 v Dunfermline AthleticDundee 0-1 Dunfermline Athletic | Betfred Cup Group D |
| 3 | 25/7/2018 | 12-0 v PeterheadPeterhead 0-2 Dundee | Betfred Cup Group D |
| 4 | 28/7/2018 | 12-0 v Brechin CityDundee 2-0 Brechin City | Betfred Cup Group D |
| 5 | 4/8/2018 | 11-2 v St MirrenSt Mirren 2-1 Dundee | Ladbrokes Premiership |
| 6 | 11/8/2018 | 10-1 v AberdeenDundee 0-1 Aberdeen | Ladbrokes Premiership |
| 7 | 18/8/2018 | 10-3 v Ayr UnitedDundee 0-3 Ayr United | Betfred Cup Second Round |
| 8 | 25/8/2018 | 10-1 v St JohnstoneSt Johnstone 1-0 Dundee | Ladbrokes Premiership |
| 9 | 1/9/2018 | 11-3 v MotherwellDundee 1-3 Motherwell | Ladbrokes Premiership |
| 10 | 15/9/2018 | 10-4 v RangersRangers 4-0 Dundee | Ladbrokes Premiership |
| 11 | 22/9/2018 | 10-3 v HibernianDundee 0-3 Hibernian | Ladbrokes Premiership |
| 12 | 6/10/2018 | 11-2 v KilmarnockDundee 1-2 Kilmarnock | Ladbrokes Premiership |
| 13 | 20/10/2018 | 10-4 v LivingstonLivingston 4-0 Dundee | Ladbrokes Premiership |
| 14 | 23/10/2018 | 10-3 v Heart of MidlothianDundee 0-3 Heart of Midlothian | Ladbrokes Premiership |
| 15 | 31/10/2018 | 10-5 v CelticDundee 0-5 Celtic | Ladbrokes Premiership |
| 16 | 3/11/2018 | 10-1 v MotherwellMotherwell 1-0 Dundee | Ladbrokes Premiership |
| 17 | 10/11/2018 | 11-1 v St MirrenDundee 1-1 St Mirren | Ladbrokes Premiership |
| 18 | 24/11/2018 | 12-2 v HibernianHibernian 2-2 Dundee | Ladbrokes Premiership |
| 19 | 5/12/2018 | 14-0 v Hamilton AcademicalDundee 4-0 Hamilton Academical | Ladbrokes Premiership |
| 20 | 9/12/2018 | 11-1 v RangersDundee 1-1 Rangers | Ladbrokes Premiership |