| Date | Competition | Fixture / Result | |
|---|
| 01 August 1998 | Scottish League Cup | Ross County 4:1 Montrose | details |
| 04 August 1998 | Scottish League Division 3 | Ross County 1:0 East Stirlingshire | details |
| 08 August 1998 | Scottish League Cup | Greenock Morton 0:1 Ross County | details |
| 15 August 1998 | Scottish League Division 3 | Albion Rovers 0:8 Ross County | details |
| 19 August 1998 | Scottish League Cup | Ross County 2:0 Dundee United | details |
| 22 August 1998 | Scottish League Division 3 | Ross County 3:1 Montrose | details |
| 29 August 1998 | Scottish League Division 3 | Ross County 2:0 Cowdenbeath | details |
| 05 September 1998 | Scottish League Division 3 | Berwick Rangers 0:2 Ross County | details |
| 09 September 1998 | Scottish League Cup | Heart of Midlothian 1:1 Ross County | details |
| 12 September 1998 | Scottish League Division 3 | Queen's Park 4:2 Ross County | details |
| 19 September 1998 | Scottish League Division 3 | Ross County 0:1 Stenhousemuir | details |
| 26 September 1998 | Scottish League Division 3 | Ross County 0:1 Brechin City | details |
| 03 October 1998 | Scottish League Division 3 | Dumbarton 1:2 Ross County | details |
| 10 October 1998 | Scottish League Division 3 | Ross County 1:2 Albion Rovers | details |
| 17 October 1998 | Scottish League Division 3 | Montrose 3:6 Ross County | details |
| 28 October 1998 | Scottish League Division 3 | Cowdenbeath 1:2 Ross County | details |
| 31 October 1998 | Scottish League Division 3 | Ross County 3:1 Berwick Rangers | details |
| 07 November 1998 | Scottish League Division 3 | Stenhousemuir 2:4 Ross County | details |
| 14 November 1998 | Scottish League Division 3 | Ross County 5:1 Queen's Park | details |
| 21 November 1998 | Scottish League Division 3 | Brechin City 0:1 Ross County | details |
| 28 November 1998 | Scottish League Division 3 | Ross County 2:0 Dumbarton | details |
| 12 December 1998 | Scottish League Division 3 | East Stirlingshire 2:2 Ross County | details |
| 19 December 1998 | Scottish League Division 3 | Ross County 3:0 Montrose | details |
| 26 December 1998 | Scottish League Division 3 | Ross County 1:0 Cowdenbeath | details |
| 09 January 1999 | Scottish Cup | Queen of the South 1:3 Ross County | details |
| 27 January 1999 | Scottish League Division 3 | Berwick Rangers 2:2 Ross County | details |
| 30 January 1999 | Scottish League Division 3 | Dumbarton 0:0 Ross County | details |
| 03 February 1999 | Scottish Cup | Clydebank 1:1 Ross County | details |
| 06 February 1999 | Scottish League Division 3 | Ross County 2:2 Stenhousemuir | details |
| 13 February 1999 | Scottish League Division 3 | Queen's Park 0:3 Ross County | details |
| 15 February 1999 | Scottish Cup | Ross County 2:3 Clydebank | details |
| 27 February 1999 | Scottish League Division 3 | Albion Rovers 3:3 Ross County | details |
| 02 March 1999 | Scottish League Division 3 | Ross County 4:2 East Stirlingshire | details |
| 06 March 1999 | Scottish League Division 3 | Ross County 6:0 Berwick Rangers | details |
| 09 March 1999 | Scottish League Division 3 | Ross County 2:1 Brechin City | details |
| 13 March 1999 | Scottish League Division 3 | Cowdenbeath 2:3 Ross County | details |
| 20 March 1999 | Scottish League Division 3 | Ross County 1:2 Dumbarton | details |
| 03 April 1999 | Scottish League Division 3 | Brechin City 0:1 Ross County | details |
| 10 April 1999 | Scottish League Division 3 | Stenhousemuir 3:2 Ross County | details |
| 17 April 1999 | Scottish League Division 3 | Ross County 1:2 Queen's Park | details |
| 24 April 1999 | Scottish League Division 3 | Montrose 2:3 Ross County | details |
| 01 May 1999 | Scottish League Division 3 | Ross County 2:0 Albion Rovers | details |
| 08 May 1999 | Scottish League Division 3 | East Stirlingshire 1:2 Ross County | details |