| Date | Competition | Fixture / Result | |
|---|
| 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 |
| 20 August 1949 | Highland League Cup | Inverness Thistle 1:1 Ross County | details |
| 24 August 1949 | Highland League Cup | Ross County 1:1 Inverness Thistle | 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 |
| 31 August 1949 | Highland League Cup | Forres Mechanics 3:4 Ross County | details |
| 03 September 1949 | Highland League | Ross County 2:1 Peterhead | details |
| 10 September 1949 | Scottish Qualifying Cup | Lossiemouth 2:3 Ross County | details |
| 17 September 1949 | Highland League | Caledonian FC 4:0 Ross County | details |
| 24 September 1949 | Scottish Qualifying Cup | Ross County 2:2 Buckie Thistle | details |
| 01 October 1949 | Scottish Qualifying Cup | Buckie Thistle 2:3 Ross County | details |
| 08 October 1949 | Highland League | Ross County 0:2 Elgin City | details |
| 15 October 1949 | Highland League | Deveronvale 3:0 Ross County | details |
| 22 October 1949 | Scottish Qualifying Cup | Ross County 1:3 Caledonian FC | details |
| 29 October 1949 | Highland League | Ross County 0:1 Fraserburgh | details |
| 05 November 1949 | Highland League | Rothes 0:3 Ross County | details |
| 12 November 1949 | Highland League | Ross County 1:1 Buckie Thistle | details |
| 19 November 1949 | Highland League | Elgin City 4:2 Ross County | details |
| 26 November 1949 | Highland League | Ross County 3:1 Inverness Clachnacuddin | details |
| 03 December 1949 | Highland League | Forres Mechanics 4:1 Ross County | details |
| 17 December 1949 | Highland League | Ross County 1:1 Rothes | details |
| 24 December 1949 | Highland League | 1st Battalion Highland Light Infantry 2:5 Ross County | details |
| 31 December 1949 | Highland League | Inverness Clachnacuddin 4:1 Ross County | details |
| 03 January 1950 | Highland League | Ross County 2:5 Caledonian FC | details |
| 07 January 1950 | Highland League | Keith 2:5 Ross County | details |
| 14 January 1950 | Highland League | Ross County 3:1 Keith | details |
| 21 January 1950 | Highland League | Lossiemouth 1:1 Ross County | details |
| 28 January 1950 | Scottish Cup | Ross County 0:3 Morton | details |
| 04 February 1950 | Highland League | Ross County 3:2 Deveronvale | details |
| 11 February 1950 | Highland League | Fraserburgh 4:2 Ross County | details |
| 25 February 1950 | North of Scotland Cup | Ross County 1:5 Inverness Clachnacuddin | details |
| 04 March 1950 | Highland League | Ross County 3:1 Lossiemouth | details |
| 11 March 1950 | Highland League | Ross County 3:1 Huntly | details |
| 18 March 1950 | Highland League | Ross County 9:1 Nairn County | details |
| 25 March 1950 | Highland League | Ross County 5:2 1st Battalion Highland Light Infantry | details |
| 01 April 1950 | Highland League | Nairn County 4:1 Ross County | details |
| 08 April 1950 | Highland League | Peterhead 3:0 Ross County | details |
| 19 April 1950 | Highland League | Inverness Thistle 2:4 Ross County | details |
| 22 April 1950 | Highland League | Ross County 2:1 Forres Mechanics | details |
| 26 April 1950 | Highland League | Ross County 3:4 Inverness Thistle | details |
| 29 April 1950 | Highland League Cup | Ross County 4:1 Buckie Thistle | details |
| 06 May 1950 | Highland League | Huntly 2:2 Ross County | details |
| 10 May 1950 | FRIENDLY | Ross County 2:2 Third Lanark | details |
| 13 May 1950 | Highland League | Buckie Thistle 6:2 Ross County | details |