| Date | Competition | Fixture / Result | |
|---|
| 26 July 2008 | Scottish Challenge Cup | Ross County 2:1 Saint Johnstone | details |
| 02 August 2008 | Scottish League Division 1 | Ross County 1:2 Dundee | details |
| 05 August 2008 | Scottish League Cup | Ross County 2:3 Airdrie United | details |
| 09 August 2008 | Scottish League Division 1 | Livingston 2:0 Ross County | details |
| 13 August 2008 | Scottish Challenge Cup | Raith Rovers 1:2 Ross County | details |
| 16 August 2008 | Scottish League Division 1 | Clyde 2:2 Ross County | details |
| 30 August 2008 | Scottish League Division 1 | Partick Thistle 0:1 Ross County | details |
| 03 September 2008 | Scottish League Division 1 | Queen of the South 1:0 Ross County | details |
| 07 September 2008 | Scottish Challenge Cup | Clyde 0:1 Ross County | details |
| 13 September 2008 | Scottish League Division 1 | Ross County 1:2 Saint Johnstone | details |
| 20 September 2008 | Scottish League Division 1 | Dunfermline Athletic 3:1 Ross County | details |
| 27 September 2008 | Scottish League Division 1 | Ross County 2:0 Airdrie United | details |
| 04 October 2008 | Scottish League Division 1 | Ross County 3:0 Greenock Morton | details |
| 12 October 2008 | Scottish Challenge Cup | Ross County 4:1 Greenock Morton | details |
| 18 October 2008 | Scottish League Division 1 | Dundee 1:2 Ross County | details |
| 25 October 2008 | Scottish League Division 1 | Ross County 0:2 Queen of the South | details |
| 01 November 2008 | Scottish League Division 1 | Ross County 3:0 Clyde | details |
| 08 November 2008 | Scottish League Division 1 | Saint Johnstone 2:1 Ross County | details |
| 16 November 2008 | Scottish Challenge Cup | Ross County 2:2 Airdrie United | details |
| 22 November 2008 | Scottish League Division 1 | Airdrie United 0:2 Ross County | details |
| 25 November 2008 | Scottish League Division 1 | Ross County 1:0 Partick Thistle | details |
| 29 November 2008 | Scottish Cup | Ross County 2:2 Dumbarton | details |
| 13 December 2008 | Scottish League Division 1 | Ross County 1:4 Livingston | details |
| 15 December 2008 | Scottish Cup | Dumbarton 1:2 Ross County | details |
| 20 December 2008 | Scottish League Division 1 | Greenock Morton 2:1 Ross County | details |
| 27 December 2008 | Scottish League Division 1 | Partick Thistle 0:2 Ross County | details |
| 10 January 2009 | Scottish Cup | Ross County 0:1 Hamilton Academical | details |
| 17 January 2009 | Scottish League Division 1 | Ross County 1:0 Queen of the South | details |
| 24 January 2009 | Scottish League Division 1 | Clyde 2:0 Ross County | details |
| 31 January 2009 | Scottish League Division 1 | Livingston 4:2 Ross County | details |
| 07 February 2009 | Scottish League Division 1 | Ross County 2:2 Saint Johnstone | details |
| 21 February 2009 | Scottish League Division 1 | Dunfermline Athletic 1:2 Ross County | details |
| 28 February 2009 | Scottish League Division 1 | Ross County 0:0 Airdrie United | details |
| 07 March 2009 | Scottish League Division 1 | Saint Johnstone 0:0 Ross County | details |
| 10 March 2009 | Scottish League Division 1 | Ross County 0:2 Partick Thistle | details |
| 14 March 2009 | Scottish League Division 1 | Dundee 2:0 Ross County | details |
| 21 March 2009 | Scottish League Division 1 | Ross County 1:1 Greenock Morton | details |
| 24 March 2009 | Scottish League Division 1 | Ross County 2:1 Dunfermline Athletic | details |
| 28 March 2009 | Scottish League Division 1 | Ross County 1:1 Dundee | details |
| 04 April 2009 | Scottish League Division 1 | Queen of the South 1:2 Ross County | details |
| 11 April 2009 | Scottish League Division 1 | Ross County 0:0 Clyde | details |
| 18 April 2009 | Scottish League Division 1 | Ross County 1:3 Dunfermline Athletic | details |
| 25 April 2009 | Scottish League Division 1 | Airdrie United 1:0 Ross County | details |
| 02 May 2009 | Scottish League Division 1 | Ross County 2:2 Livingston | details |
| 09 May 2009 | Scottish League Division 1 | Greenock Morton 0:2 Ross County | details |