| Starting Appearances - Bill Simpson | Starting | Sub (Used) | Sub (Unused) | All | ||
|---|---|---|---|
| 13 August 1949 | Highland League Cup | Ross County 6:2 Inverness Clachnacuddin | details |
| 16 August 1949 | Highland League Cup | Inverness Clachnacuddin 2:3 Ross County | details |
| 25 August 1949 | Highland League Cup | Inverness Thistle 1:1 Ross County | details |
| 27 August 1949 | Highland League Cup | Ross County 2:1 Inverness Thistle | details |
| 19 November 1949 | Highland League | Elgin City 4:2 Ross County | details |