| Starting Appearances - John McGlashan | Starting | Sub (Used) | Sub (Unused) | All |
|---|
| 10 July 1999 | FRIENDLY | Huntly 0:1 Ross County | details |
| 13 July 1999 | FRIENDLY | Ross County 0:1 Dunfermline Athletic | details |
| 16 July 1999 | FRIENDLY | Scalloway 2:8 Ross County | details |
| 21 July 1999 | FRIENDLY | Deveronvale 0:1 Ross County | details |
| 24 July 1999 | FRIENDLY | Ross County 2:0 Livingston | details |
| 31 July 1999 | Scottish League Cup | Ross County 2:1 Forfar Athletic | details |
| 07 August 1999 | Scottish League Division 2 | Ross County 2:1 Hamilton Academical | details |
| 10 August 1999 | Scottish Challenge Cup | Clyde 0:4 Ross County | details |
| 14 August 1999 | Scottish League Division 2 | Stranraer 0:0 Ross County | details |
| 18 August 1999 | Scottish League Cup | Dundee United 3:1 Ross County | details |
| 21 August 1999 | Scottish League Division 2 | Ross County 0:0 Stenhousemuir | 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 |
| 28 March 2000 | Scottish League Division 2 | Ross County 2:0 Stenhousemuir | details |
| 01 April 2000 | Scottish League Division 2 | Ross County 5:1 Stirling Albion | details |
| 08 April 2000 | Scottish League Division 2 | Ross County 1:3 Partick Thistle | details |
| 15 April 2000 | Scottish League Division 2 | Queen of the South 0:3 Ross County | details |
| 22 April 2000 | Scottish League Division 2 | Hamilton Academical 0:3 Ross County | details |
| 29 April 2000 | Scottish League Division 2 | Ross County 3:1 Stranraer | details |
| 06 May 2000 | Scottish League Division 2 | Stenhousemuir 2:2 Ross County | details |