| Starting Appearances - David Winters | Starting | Sub (Used) | Sub (Unused) | All |
|---|
| 02 August 2003 | Scottish Challenge Cup | Cowdenbeath 1:2 Ross County | details |
| 09 August 2003 | Scottish League Division 1 | Ross County 4:0 Brechin City | details |
| 12 August 2003 | Scottish Challenge Cup | Ross County 5:0 Dumbarton | details |
| 16 August 2003 | Scottish League Division 1 | Queen of the South 1:0 Ross County | details |
| 23 August 2003 | Scottish League Division 1 | Ross County 2:0 Saint Mirren | details |
| 26 August 2003 | Scottish Challenge Cup | Inverness Caledonian Thistle 1:0 Ross County | details |
| 30 August 2003 | Scottish League Division 1 | Ross County 1:1 Inverness Caledonian Thistle | details |
| 13 September 2003 | Scottish League Division 1 | Falkirk 0:2 Ross County | details |
| 20 September 2003 | Scottish League Division 1 | Ross County 2:2 Ayr United | details |
| 27 September 2003 | Scottish League Division 1 | Raith Rovers 1:7 Ross County | details |
| 04 October 2003 | Scottish League Division 1 | Clyde 2:2 Ross County | details |
| 18 October 2003 | Scottish League Division 1 | Ross County 0:3 Saint Johnstone | details |
| 26 October 2003 | Scottish League Division 1 | Ross County 1:0 Queen of the South | details |
| 01 November 2003 | Scottish League Division 1 | Brechin City 4:2 Ross County | details |
| 14 November 2003 | Scottish League Division 1 | Inverness Caledonian Thistle 3:3 Ross County | details |
| 22 November 2003 | Scottish League Division 1 | Ross County 3:2 Raith Rovers | details |
| 29 November 2003 | Scottish League Division 1 | Ayr United 1:3 Ross County | details |
| 06 December 2003 | Scottish League Division 1 | Saint Johnstone 1:1 Ross County | details |
| 03 January 2004 | Scottish League Division 1 | Ross County 1:0 Inverness Caledonian Thistle | details |
| 10 January 2004 | Scottish Cup | Celtic 2:0 Ross County | details |
| 17 January 2004 | Scottish League Division 1 | Falkirk 2:0 Ross County | details |
| 24 January 2004 | Scottish League Division 1 | Ross County 1:1 Ayr United | details |
| 14 February 2004 | Scottish League Division 1 | Clyde 1:0 Ross County | details |
| 20 March 2004 | Scottish League Division 1 | Ross County 1:1 Falkirk | details |
| 27 March 2004 | Scottish League Division 1 | Inverness Caledonian Thistle 1:0 Ross County | details |
| 01 May 2004 | Scottish League Division 1 | Brechin City 1:0 Ross County | details |