| Date | Competition | Fixture / Result | |
|---|
| 12 August 1939 | Inverness Sports Bed Cup | Inverness Clachnacuddin 2:0 Ross County | details |
| 19 August 1939 | Highland League | Elgin City 2:2 Ross County | details |
| 26 August 1939 | Highland League | Inverness Thistle 2:2 Ross County | details |
| 31 August 1939 | Inverness Cup | Inverness Thistle 3:1 Ross County | details |
| 07 October 1939 | Highland Emergency League | Ross County 2:2 Inverness Thistle | details |
| 14 October 1939 | Highland Emergency League | Nairn County 0:3 Ross County | details |
| 21 October 1939 | Highland Emergency League | Ross County 0:1 Nairn County | details |
| 04 November 1939 | Highland Emergency League | Caledonian FC 0:3 Ross County | details |
| 11 November 1939 | Highland Emergency League | Ross County 5:4 Inverness Clachnacuddin | details |
| 18 November 1939 | Highland Emergency League | Ross County 4:2 Caledonian FC | details |
| 25 November 1939 | Highland Emergency League | Services XI 1:1 Ross County | details |
| 09 December 1939 | Highland Emergency League | Inverness Clachnacuddin 6:1 Ross County | details |
| 02 March 1940 | Highland Emergency League | Army XI 4:3 Ross County | details |
| 09 March 1940 | Highland Emergency League | Ross County 4:5 Army XI | details |
| 16 March 1940 | Ness Cup | Ross County 4:3 Services XI | details |
| 30 March 1940 | Ness Cup | Services XI 4:4 Ross County | details |
| 06 April 1940 | Ness Cup | Ross County 1:3 Royal Artillery Mountain Battery | details |
| 13 April 1940 | Ness Cup | Royal Artillery Mountain Battery 3:6 Ross County | details |
| 20 April 1940 | Ness Cup | Inverness Thistle 3:5 Ross County | details |
| 27 April 1940 | Ness Cup | Ross County 3:0 Inverness Thistle | details |
| 04 May 1940 | Ness Cup | Ross County 1:8 Army XI | details |
| 18 May 1940 | North of Scotland Cup | Inverness Thistle 6:6 Ross County | details |
| 22 May 1940 | North of Scotland Cup | Ross County 3:1 Inverness Thistle | details |
| 25 May 1940 | North of Scotland Cup | Inverness Clachnacuddin 3:2 Ross County | details |
| 29 May 1940 | Highland Emergency League | Inverness Thistle 3:2 Ross County | details |