| 1 | Sat 14 Jul 2018 | 21-1 v ArbroathDundee United 1-1 Arbroath | Betfred Cup Group A |
| 2 | Tue 17 Jul 2018 | 20-1 v Ross CountyRoss County 1-0 Dundee United | Betfred Cup Group A |
| 3 | Sat 21 Jul 2018 | 21-1 v Alloa AthleticDundee United 1-1 Alloa Athletic | Betfred Cup Group A |
| 4 | Sat 25 Aug 2018 | 23-1 v Partick ThistleDundee United 3-1 Partick Thistle | Ladbrokes Championship |
| 5 | Sat 1 Sep 2018 | 2 1-1 v Alloa AthleticAlloa Athletic 1-1 Dundee United | Ladbrokes Championship |
| 6 | Sat 29 Sep 2018 | 2 1-5 v Ross CountyDundee United 1-5 Ross County | Ladbrokes Championship |
| 7 | Sat 20 Oct 2018 | 21-1 v Inverness Caledonian ThistleDundee United 1-1 Inverness Caledonian Thistle | Ladbrokes Championship |
| 8 | Sat 27 Oct 2018 | 22-0 v Dunfermline AthleticDunfermline Athletic 0-2 Dundee United | Ladbrokes Championship |
| 9 | Sat 3 Nov 2018 | 22-0 v Queen of the SouthDundee United 2-0 Queen of the South | Ladbrokes Championship |
| 10 | Sat 10 Nov 2018 | 2 1-0 v Ross CountyRoss County 0-1 Dundee United | Ladbrokes Championship |
| 11 | Tue 20 Nov 2018 | 24-2 v Alloa AthleticDundee United 4-2 Alloa Athletic | Ladbrokes Championship |
| 12 | Sat 8 Dec 2018 | 21-1 v Greenock MortonGreenock Morton 1-1 Dundee United | Ladbrokes Championship |
| 13 | Sat 15 Dec 2018 | 21-1 v Inverness Caledonian ThistleInverness Caledonian Thistle 1-1 Dundee United | Ladbrokes Championship |
| 14 | Sat 22 Dec 2018 | 22-1 v FalkirkDundee United 2-1 Falkirk | Ladbrokes Championship |
| 15 | Sat 29 Dec 2018 | 2 1-2 v Alloa AthleticAlloa Athletic 2-1 Dundee United | Ladbrokes Championship |
| 16 | Sat 5 Jan 2019 | 21-1 v Partick ThistleDundee United 1-1 Partick Thistle | Ladbrokes Championship |
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