| 1 | Sat 12 Jan 2019 | 0-4 v Queen of the SouthQueen of the South 4-0 Ross County | Ladbrokes Championship |
| 2 | Sat 19 Jan 2019 | 2-1 v MotherwellMotherwell 1-2 Ross County | William Hill Scottish Cup Fourth Round |
| 3 | Sat 26 Jan 2019 | 2-0 v Alloa AthleticRoss County 2-0 Alloa Athletic | Ladbrokes Championship |
| 4 | Sat 2 Feb 2019 | 2-1 v Dunfermline AthleticDunfermline Athletic 1-2 Ross County | Ladbrokes Championship |
| 5 | Mon 11 Feb 2019 | 2-2 v Inverness Caledonian ThistleRoss County 2-2 Inverness Caledonian Thistle | William Hill Scottish Cup Fifth Round |
| 6 | Tue 19 Feb 2019 | 2-2 v Inverness Caledonian ThistleInverness Caledonian Thistle 2-2 Ross County | William Hill Scottish Cup Fifth Round Replay |
| 7 | Sat 23 Feb 2019 | 4-2 v Partick ThistlePartick Thistle 2-4 Ross County | Ladbrokes Championship |
| 8 | Tue 26 Feb 2019 | 3-2 v Ayr UnitedRoss County 3-2 Ayr United | Ladbrokes Championship |
| 9 | Sat 9 Mar 2019 | 2-0 v Greenock MortonRoss County 2-0 Greenock Morton | Ladbrokes Championship |
| 10 | Tue 12 Mar 2019 | 2-1 v FalkirkRoss County 2-1 Falkirk | Ladbrokes Championship |
| 11 | Tue 19 Mar 2019 | 0-1 v Dundee UnitedDundee United 1-0 Ross County | Ladbrokes Championship |
| 12 | Sat 30 Mar 2019 | 0-1 v Alloa AthleticAlloa Athletic 1-0 Ross County | Ladbrokes Championship |
| 13 | Tue 2 Apr 2019 | 2-1 v Inverness Caledonian ThistleInverness Caledonian Thistle 1-2 Ross County | Ladbrokes Championship |
| 14 | Fri 5 Apr 2019 | 1-1 v Dundee UnitedRoss County 1-1 Dundee United | Ladbrokes Championship |
| 15 | Tue 9 Apr 2019 | 1-0 v Dunfermline AthleticRoss County 1-0 Dunfermline Athletic | Ladbrokes Championship |
| 16 | Sat 13 Apr 2019 | 0-0 v Partick ThistleRoss County 0-0 Partick Thistle | Ladbrokes Championship |
| 17 | Fri 19 Apr 2019 | 3-1 v Ayr UnitedAyr United 1-3 Ross County | Ladbrokes Championship |
| 18 | Sat 4 May 2019 | 2-3 v FalkirkFalkirk 3-2 Ross County | Ladbrokes Championship |
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