| Starting Appearances - Garry Wood | Starting | Sub (Used) | Sub (Unused) | All |
|---|
| 13 July 1999 | FRIENDLY | Ross County 0:1 Dunfermline Athletic | details |
| 28 July 1999 | FRIENDLY | Elgin City 1:3 Ross County | details |
| 21 August 1999 | Scottish League Division 2 | Ross County 0:0 Stenhousemuir | details |
| 24 August 1999 | Scottish Challenge Cup | Ross County 3:0 Greenock Morton | details |
| 28 August 1999 | Scottish League Division 2 | Ross County 2:0 Arbroath | details |
| 14 September 1999 | Scottish Challenge Cup | Ross County 1:2 Alloa Athletic | details |
| 18 September 1999 | Scottish League Division 2 | Ross County 2:0 Clyde | details |
| 25 September 1999 | Scottish League Division 2 | Partick Thistle 0:2 Ross County | details |
| 02 October 1999 | Scottish League Division 2 | Ross County 1:1 Queen of the South | details |
| 09 October 1999 | Scottish League Division 2 | Hamilton Academical 1:0 Ross County | details |
| 06 November 1999 | Scottish League Division 2 | Clyde 3:1 Ross County | details |
| 12 November 1999 | Scottish League Division 2 | Ross County 1:3 Stirling Albion | details |
| 11 December 1999 | Scottish Cup | Ross County 2:2 Forfar Athletic | details |