| 1 | Sat 2 Feb 2019 | 3-1 v Alloa AthleticAlloa Athletic 1-3 Ayr United | Ladbrokes Championship |
| 2 | Sat 16 Feb 2019 | 0-0 v Greenock MortonGreenock Morton 0-0 Ayr United | Ladbrokes Championship |
| 3 | Sat 23 Feb 2019 | 0-1 v Dunfermline AthleticAyr United 0-1 Dunfermline Athletic | Ladbrokes Championship |
| 4 | Tue 26 Feb 2019 | 2-3 v Ross CountyRoss County 3-2 Ayr United | Ladbrokes Championship |
| 5 | Fri 8 Mar 2019 | 0-2 v FalkirkFalkirk 2-0 Ayr United | Ladbrokes Championship |
| 6 | Fri 29 Mar 2019 | 1-0 v Dunfermline AthleticDunfermline Athletic 0-1 Ayr United | Ladbrokes Championship |
| 7 | Sat 6 Apr 2019 | 0-1 v Inverness Caledonian ThistleAyr United 0-1 Inverness Caledonian Thistle | Ladbrokes Championship |
| 8 | Tue 9 Apr 2019 | 1-0 v Queen of the SouthAyr United 1-0 Queen of the South | Ladbrokes Championship |
| 9 | Fri 12 Apr 2019 | 1-2 v Dundee UnitedDundee United 2-1 Ayr United | Ladbrokes Championship |
| 10 | Fri 19 Apr 2019 | 1-3 v Ross CountyAyr United 1-3 Ross County | Ladbrokes Championship |
| 11 | Tue 23 Apr 2019 | 0-1 v Partick ThistleAyr United 0-1 Partick Thistle | Ladbrokes Championship |
| 12 | Sat 27 Apr 2019 | 2-1 v Partick ThistlePartick Thistle 1-2 Ayr United | Ladbrokes Championship |
| 13 | Sat 4 May 2019 | 1-1 v Alloa AthleticAyr United 1-1 Alloa Athletic | Ladbrokes Championship |
| 14 | Sat 11 May 2019 | 1-1 v Inverness Caledonian ThistleInverness Caledonian Thistle 1-1 Ayr United | Ladbrokes Championship Play-off |
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