| 1 | Sat 6 Oct 2018 | 10-2 v Ayr UnitedAyr United 2-0 Dundee United |
| 2 | Sat 13 Oct 2018 | 12-1 v Partick ThistlePartick Thistle 1-2 Dundee United |
| 3 | Sat 20 Oct 2018 | 11-1 v Inverness Caledonian ThistleDundee United 1-1 Inverness Caledonian Thistle |
| 4 | Sat 27 Oct 2018 | 12-0 v Dunfermline AthleticDunfermline Athletic 0-2 Dundee United |
| 5 | Sat 3 Nov 2018 | 12-0 v Queen of the SouthDundee United 2-0 Queen of the South |
| 6 | Sat 10 Nov 2018 | 11-0 v Ross CountyRoss County 0-1 Dundee United |
| 7 | Tue 20 Nov 2018 | 14-2 v Alloa AthleticDundee United 4-2 Alloa Athletic |
| 8 | Fri 30 Nov 2018 | 10-5 v Ayr UnitedDundee United 0-5 Ayr United |
| 9 | Sat 15 Dec 2018 | 11-1 v Inverness Caledonian ThistleInverness Caledonian Thistle 1-1 Dundee United |
| 10 | Sat 22 Dec 2018 | 12-1 v FalkirkDundee United 2-1 Falkirk |
| 11 | Sat 29 Dec 2018 | 11-2 v Alloa AthleticAlloa Athletic 2-1 Dundee United |
| 12 | Sat 5 Jan 2019 | 11-1 v Partick ThistleDundee United 1-1 Partick Thistle |
| 13 | Sat 2 Feb 2019 | 12-1 v Greenock MortonDundee United 2-1 Greenock Morton |
| 14 | Sat 16 Feb 2019 | 11-0 v Queen of the SouthQueen of the South 0-1 Dundee United |
| 15 | Sat 23 Feb 2019 | 11-1 v FalkirkFalkirk 1-1 Dundee United |
| 16 | Tue 26 Feb 2019 | 11-0 v Inverness Caledonian ThistleDundee United 1-0 Inverness Caledonian Thistle |
| 17 | Sat 9 Mar 2019 | 11-2 v Partick ThistlePartick Thistle 2-1 Dundee United |
| 18 | Tue 19 Mar 2019 | 11-0 v Ross CountyDundee United 1-0 Ross County |
| 19 | Sat 23 Mar 2019 | 12-1 v Alloa AthleticDundee United 2-1 Alloa Athletic |
| 20 | Tue 26 Mar 2019 | 11-0 v Dunfermline AthleticDunfermline Athletic 0-1 Dundee United |
| 21 | Sat 30 Mar 2019 | 11-2 v Queen of the SouthDundee United 1-2 Queen of the South |
| 22 | Fri 5 Apr 2019 | 11-1 v Ross CountyRoss County 1-1 Dundee United |
| 23 | Fri 12 Apr 2019 | 12-1 v Ayr UnitedDundee United 2-1 Ayr United |
| 24 | Sat 20 Apr 2019 | 12-0 v Inverness Caledonian ThistleInverness Caledonian Thistle 0-2 Dundee United |
| 25 | Sat 27 Apr 2019 | 12-0 v FalkirkDundee United 2-0 Falkirk |
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