| 1 | Sat 14 Jul 2018 | 1-3 v Ayr UnitedAyr United 3-1 Greenock Morton | Betfred Cup Group E |
| 2 | Tue 17 Jul 2018 | 1-2 v Partick ThistlePartick Thistle 2-1 Greenock Morton | Betfred Cup Group E |
| 3 | Sat 21 Jul 2018 | 2-0 v StenhousemuirGreenock Morton 2-0 Stenhousemuir | Betfred Cup Group E |
| 4 | Sat 11 Aug 2018 | 232-0 v Alloa AthleticAlloa Athletic 0-2 Greenock Morton | Ladbrokes Championship |
| 5 | Sat 25 Aug 2018 | 232-1 v Ross CountyGreenock Morton 2-1 Ross County | Ladbrokes Championship |
| 6 | Sat 1 Sep 2018 | 230-1 v Partick ThistlePartick Thistle 1-0 Greenock Morton | Ladbrokes Championship |
| 7 | Sat 15 Sep 2018 | 231-1 v Dundee UnitedDundee United 1-1 Greenock Morton | Ladbrokes Championship |
| 8 | Sat 22 Sep 2018 | 231-1 v Dunfermline AthleticGreenock Morton 1-1 Dunfermline Athletic | Ladbrokes Championship |
| 9 | Sat 29 Sep 2018 | 231-5 v Ayr UnitedGreenock Morton 1-5 Ayr United | Ladbrokes Championship |
| 10 | Sat 6 Oct 2018 | 231-1 v Inverness Caledonian ThistleInverness Caledonian Thistle 1-1 Greenock Morton | Ladbrokes Championship |
| 11 | Sat 20 Oct 2018 | 231-0 v FalkirkGreenock Morton 1-0 Falkirk | Ladbrokes Championship |
| 12 | Sat 27 Oct 2018 | 230-5 v Ross CountyRoss County 5-0 Greenock Morton | Ladbrokes Championship |
| 13 | Fri 4 Jan 2019 | 231-0 v Ross CountyGreenock Morton 1-0 Ross County | Ladbrokes Championship |
| 14 | Sat 12 Jan 2019 | 23 1-2 v Alloa AthleticAlloa Athletic 2-1 Greenock Morton | Ladbrokes Championship |
| 15 | Sat 2 Feb 2019 | 1-2 v Ross CountyDunfermline Athletic 1-2 Ross County | Ladbrokes Championship |
| 16 | Sat 16 Feb 2019 | 1-0 v Inverness Caledonian ThistleDunfermline Athletic 1-0 Inverness Caledonian Thistle | Ladbrokes Championship |
| 17 | Sat 23 Feb 2019 | 1-0 v Ayr UnitedAyr United 0-1 Dunfermline Athletic | Ladbrokes Championship |
| 18 | Tue 26 Feb 2019 | 3-0 v Partick ThistleDunfermline Athletic 3-0 Partick Thistle | Ladbrokes Championship |
| 19 | Sat 2 Mar 2019 | 1-0 v Queen of the SouthDunfermline Athletic 1-0 Queen of the South | Ladbrokes Championship |
| 20 | Sat 9 Mar 2019 | 1-0 v Alloa AthleticAlloa Athletic 0-1 Dunfermline Athletic | Ladbrokes Championship |
| 21 | Tue 26 Mar 2019 | 0-1 v Dundee UnitedDunfermline Athletic 0-1 Dundee United | Ladbrokes Championship |
| 22 | Fri 29 Mar 2019 | 0-1 v Ayr UnitedDunfermline Athletic 0-1 Ayr United | Ladbrokes Championship |
| 23 | Sat 6 Apr 2019 | 2-2 v Partick ThistlePartick Thistle 2-2 Dunfermline Athletic | Ladbrokes Championship |
| 24 | Tue 9 Apr 2019 | 0-1 v Ross CountyRoss County 1-0 Dunfermline Athletic | Ladbrokes Championship |
| 25 | Sat 13 Apr 2019 | 0-1 v FalkirkDunfermline Athletic 0-1 Falkirk | Ladbrokes Championship |
| 26 | Sat 20 Apr 2019 | 1-2 v Queen of the SouthQueen of the South 2-1 Dunfermline Athletic | Ladbrokes Championship |
| 27 | Sat 27 Apr 2019 | 0-1 v Greenock MortonDunfermline Athletic 0-1 Greenock Morton | Ladbrokes Championship |
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