| Date | Competition | Fixture / Result | |
|---|
| 09 August 1958 | Highland League Cup | Ross County 2:4 Inverness Clachnacuddin | details |
| 13 August 1958 | Highland League Cup | Ross County 2:5 Inverness Thistle | details |
| 16 August 1958 | Highland League Cup | Caledonian FC 1:3 Ross County | details |
| 20 August 1958 | Highland League Cup | Ross County 3:0 Caledonian FC | details |
| 23 August 1958 | Highland League Cup | Inverness Clachnacuddin 0:2 Ross County | details |
| 25 August 1958 | FRIENDLY | Ross County 5:1 Highland League Select | details |
| 27 August 1958 | Highland League Cup | Inverness Thistle 1:1 Ross County | details |
| 30 August 1958 | Highland League | Rothes 1:0 Ross County | details |
| 06 September 1958 | Highland League | Ross County 1:1 Fraserburgh | details |
| 13 September 1958 | Highland League | Huntly 3:4 Ross County | details |
| 20 September 1958 | Scottish Qualifying Cup | Caledonian FC 2:2 Ross County | details |
| 27 September 1958 | Scottish Qualifying Cup | Ross County 2:1 Caledonian FC | details |
| 04 October 1958 | Scottish Qualifying Cup | Huntly 1:4 Ross County | details |
| 11 October 1958 | Highland League | Ross County 5:2 Deveronvale | details |
| 18 October 1958 | Highland League | Inverness Clachnacuddin 2:3 Ross County | details |
| 25 October 1958 | Scottish Qualifying Cup | Ross County 1:3 Fraserburgh | details |
| 01 November 1958 | Highland League | Ross County 1:2 Peterhead | details |
| 08 November 1958 | Highland League | Deveronvale 3:2 Ross County | details |
| 15 November 1958 | Highland League | Ross County 5:0 Nairn County | details |
| 22 November 1958 | FRIENDLY | Sutherland Select 1:5 Ross County | details |
| 29 November 1958 | Highland League | Caledonian FC 2:1 Ross County | details |
| 06 December 1958 | Highland League | Ross County 2:2 Elgin City | details |
| 13 December 1958 | Highland League | Inverness Thistle 8:1 Ross County | details |
| 20 December 1958 | Highland League | Ross County 1:2 Inverness Clachnacuddin | details |
| 03 January 1959 | Highland League | Nairn County 4:1 Ross County | details |
| 10 January 1959 | Highland League | Ross County 0:1 Keith | details |
| 24 January 1959 | Highland League | Ross County 3:0 Lossiemouth | details |
| 31 January 1959 | Scottish Cup | Peebles Rovers 2:0 Ross County | details |
| 07 February 1959 | North of Scotland Cup | Inverness Thistle 1:0 Ross County | details |
| 21 February 1959 | Highland League | Ross County 5:2 Rothes | details |
| 28 February 1959 | Highland League | Fraserburgh 1:2 Ross County | details |
| 07 March 1959 | Highland League | Ross County 2:1 Huntly | details |
| 14 March 1959 | Highland League | Buckie Thistle 0:1 Ross County | details |
| 21 March 1959 | Highland League | Keith 0:2 Ross County | details |
| 28 March 1959 | Highland League | Ross County 4:2 Forres Mechanics | details |
| 04 April 1959 | Highland League | Forres Mechanics 6:1 Ross County | details |
| 11 April 1959 | FRIENDLY | Ross County 1:1 East Fife | details |
| 15 April 1959 | Highland League | Elgin City 4:2 Ross County | details |
| 18 April 1959 | Highland League | Lossiemouth 4:0 Ross County | details |
| 25 April 1959 | Highland League | Ross County 2:5 Buckie Thistle | details |
| 29 April 1959 | Highland League | Ross County 0:1 Inverness Thistle | details |
| 02 May 1959 | Highland League | Peterhead 2:1 Ross County | details |
| 09 May 1959 | Highland League | Ross County 2:1 Caledonian FC | details |