| Date | Competition | Fixture / Result | |
|---|
| 20 April 1994 | Highland League | Ross County 4:3 Caledonian FC | details |
| 12 February 1994 | North of Scotland Cup | Ross County 0:1 Caledonian FC | details |
| 05 February 1994 | North of Scotland Cup | Caledonian FC 1:1 Ross County | details |
| 27 October 1993 | Highland League | Caledonian FC 5:2 Ross County | details |
| 16 August 1993 | Highland League Cup | Caledonian FC 4:3 Ross County | details |
| 11 August 1993 | Highland League Cup | Ross County 1:1 Caledonian FC | details |
| 10 April 1993 | Highland League | Caledonian FC 2:1 Ross County | details |
| 21 November 1992 | Highland League | Ross County 4:1 Caledonian FC | details |
| 18 April 1992 | Highland League | Ross County 3:1 Caledonian FC | details |
| 29 February 1992 | North of Scotland Cup | Ross County 2:0 Caledonian FC | details |
| 26 November 1991 | Inverness Cup | Caledonian FC 2:3 Ross County | details |
| 26 October 1991 | Scottish Qualifying Cup | Ross County 1:2 Caledonian FC | details |
| 19 October 1991 | Highland League | Caledonian FC 4:0 Ross County | details |
| 21 August 1991 | Highland League Cup | Ross County 2:0 Caledonian FC | details |
| 20 March 1991 | Highland League | Caledonian FC 1:1 Ross County | details |
| 10 October 1990 | Highland League | Ross County 3:2 Caledonian FC | details |
| 13 August 1990 | Highland League Cup | Ross County 2:2 Caledonian FC | details |
| 11 August 1990 | Highland League Cup | Caledonian FC 1:1 Ross County | details |
| 28 March 1990 | Highland League | Caledonian FC 1:0 Ross County | details |
| 03 October 1989 | Highland League | Ross County 0:3 Caledonian FC | details |
| 28 April 1989 | Highland League | Caledonian FC 0:1 Ross County | details |
| 27 December 1988 | Highland League | Ross County 5:1 Caledonian FC | details |
| 30 November 1988 | Inverness Cup | Ross County 0:2 Caledonian FC | details |
| 24 August 1988 | Highland League Cup | Ross County 0:5 Caledonian FC | details |
| 18 November 1987 | Highland League | Ross County 0:2 Caledonian FC | details |
| 27 October 1987 | Inverness Cup | Caledonian FC 3:2 Ross County | details |
| 12 September 1987 | Highland League | Caledonian FC 3:1 Ross County | details |
| 15 August 1987 | Highland League Cup | Caledonian FC 3:0 Ross County | details |
| 11 March 1987 | Highland League | Caledonian FC 3:0 Ross County | details |
| 25 November 1986 | Inverness Cup | Ross County 1:5 Caledonian FC | details |
| 24 September 1986 | Highland League | Ross County 0:1 Caledonian FC | details |
| 19 October 1985 | Highland League | Ross County 0:2 Caledonian FC | details |
| 07 September 1985 | Scottish Qualifying Cup | Caledonian FC 3:0 Ross County | details |
| 21 August 1985 | Highland League Cup | Caledonian FC 0:1 Ross County | details |
| 07 August 1985 | Highland League | Caledonian FC 1:1 Ross County | details |
| 26 March 1985 | Highland League | Caledonian FC 1:2 Ross County | details |
| 24 November 1984 | Highland League | Ross County 1:1 Caledonian FC | details |
| 11 August 1984 | Highland League Cup | Caledonian FC 5:0 Ross County | details |
| 07 March 1984 | Highland League | Caledonian FC 0:2 Ross County | details |
| 25 February 1984 | North of Scotland Cup | Ross County 1:3 Caledonian FC | details |
| 03 September 1983 | Highland League | Caledonian FC 1:3 Ross County | details |
| 23 April 1983 | Highland League | Caledonian FC 2:1 Ross County | details |
| 08 September 1982 | Highland League | Ross County 1:3 Caledonian FC | details |
| 16 March 1982 | Highland League | Ross County 1:4 Caledonian FC | details |
| 06 February 1982 | Highland League | Caledonian FC 0:0 Ross County | details |
| 04 November 1981 | Inverness Cup | Caledonian FC 1:2 Ross County | details |
| 05 August 1981 | Highland League Cup | Caledonian FC 2:1 Ross County | details |
| 23 March 1981 | Highland League | Caledonian FC 1:0 Ross County | details |
| 09 September 1980 | Highland League | Ross County 1:0 Caledonian FC | details |
| 22 March 1980 | Highland League | Caledonian FC 4:4 Ross County | details |
| 07 November 1979 | Inverness Cup | Ross County 5:4 Caledonian FC | details |
| 29 September 1979 | Highland League | Ross County 6:2 Caledonian FC | details |
| 20 August 1979 | Highland League Cup | Caledonian FC 1:2 Ross County | details |
| 15 August 1979 | Highland League Cup | Ross County 1:1 Caledonian FC | details |
| 03 August 1979 | Bell's Scotch Cup | Ross County 2:3 Caledonian FC | details |
| 04 April 1979 | Highland League | Ross County 1:3 Caledonian FC | details |
| 22 January 1979 | FRIENDLY | Ross County 2:1 Caledonian FC | details |
| 28 October 1978 | Highland League | Caledonian FC 0:2 Ross County | details |
| 24 October 1978 | Inverness Cup | Caledonian FC 1:2 Ross County | details |
| 23 September 1978 | Scottish Qualifying Cup | Ross County 0:5 Caledonian FC | details |
| 16 September 1978 | Scottish Qualifying Cup | Caledonian FC 1:1 Ross County | details |
| 04 May 1978 | Highland League | Caledonian FC 6:3 Ross County | details |
| 25 March 1978 | North of Scotland Cup | Caledonian FC 6:1 Ross County | details |
| 03 September 1977 | Highland League | Ross County 3:0 Caledonian FC | details |
| 09 April 1977 | North of Scotland Cup | Ross County 0:3 Caledonian FC | details |
| 16 February 1977 | Highland League | Caledonian FC 2:1 Ross County | details |
| 06 November 1976 | Highland League | Ross County 3:2 Caledonian FC | details |
| 18 August 1976 | Highland League Cup | Caledonian FC 3:1 Ross County | details |
| 07 April 1976 | Highland League | Caledonian FC 3:1 Ross County | details |
| 28 February 1976 | North of Scotland Cup | Caledonian FC 2:3 Ross County | details |
| 25 October 1975 | Highland League | Ross County 2:2 Caledonian FC | details |
| 20 August 1975 | Highland League Cup | Ross County 4:1 Caledonian FC | details |
| 23 April 1975 | Highland League | Caledonian FC 3:0 Ross County | details |
| 22 March 1975 | North of Scotland Cup | Ross County 1:2 Caledonian FC | details |
| 15 March 1975 | North of Scotland Cup | Caledonian FC 1:1 Ross County | details |
| 09 November 1974 | Highland League | Ross County 2:1 Caledonian FC | details |
| 31 August 1974 | Highland League Cup | Caledonian FC 1:2 Ross County | details |
| 08 December 1973 | Highland League | Ross County 3:3 Caledonian FC | details |
| 20 October 1973 | Highland League | Caledonian FC 0:2 Ross County | details |
| 08 August 1973 | Highland League Cup | Ross County 3:2 Caledonian FC | details |
| 08 May 1973 | Drybrough Highland Cup | Caledonian FC 1:3 Ross County | details |
| 07 April 1973 | North of Scotland Cup | Ross County 5:2 Caledonian FC | details |
| 27 January 1973 | Highland League | Ross County 1:1 Caledonian FC | details |
| 18 December 1972 | Bell's Scotch Cup | Caledonian FC 1:2 Ross County | details |
| 02 December 1972 | Highland League | Caledonian FC 3:3 Ross County | details |
| 17 August 1972 | Highland League Cup | Caledonian FC 1:5 Ross County | details |
| 04 March 1972 | Highland League | Ross County 0:3 Caledonian FC | details |
| 19 February 1972 | North of Scotland Cup | Caledonian FC 0:3 Ross County | details |
| 08 January 1972 | Highland League | Caledonian FC 3:1 Ross County | details |
| 05 August 1971 | FRIENDLY | Ross County 1:2 Caledonian FC | details |
| 27 March 1971 | Highland League | Caledonian FC 4:3 Ross County | details |
| 06 February 1971 | Highland League | Ross County 3:2 Caledonian FC | details |
| 03 October 1970 | Scottish Qualifying Cup | Ross County 3:0 Caledonian FC | details |
| 19 August 1970 | Highland League Cup | Caledonian FC 2:3 Ross County | details |
| 12 August 1970 | Highland League Cup | Ross County 1:3 Caledonian FC | details |
| 15 May 1970 | Highland League | Ross County 1:0 Caledonian FC | details |
| 22 April 1970 | Highland League | Caledonian FC 0:1 Ross County | details |
| 20 December 1969 | Scottish Cup | Caledonian FC 5:0 Ross County | details |
| 15 November 1969 | Scottish Qualifying Cup | Ross County 1:4 Caledonian FC | details |
| 08 November 1969 | Scottish Qualifying Cup | Caledonian FC 1:1 Ross County | details |
| 27 August 1969 | Highland League Cup | Caledonian FC 4:2 Ross County | details |
| 18 January 1969 | Highland League | Caledonian FC 2:0 Ross County | details |
| 05 October 1968 | Highland League | Ross County 2:2 Caledonian FC | details |
| 02 March 1968 | Highland League | Ross County 3:2 Caledonian FC | details |
| 02 December 1967 | Highland League | Caledonian FC 4:0 Ross County | details |
| 23 August 1967 | Highland League Cup | Ross County 0:1 Caledonian FC | details |
| 16 August 1967 | Highland League Cup | Caledonian FC 3:2 Ross County | details |
| 12 April 1967 | Highland League | Caledonian FC 2:4 Ross County | details |
| 05 April 1967 | Highland League | Ross County 5:0 Caledonian FC | details |
| 14 December 1966 | Inverness Cup | Ross County 2:1 Caledonian FC | details |
| 01 September 1966 | Highland League Cup | Ross County 1:4 Caledonian FC | details |
| 20 April 1966 | Highland League | Caledonian FC 2:2 Ross County | details |
| 13 April 1966 | Highland League | Ross County 0:2 Caledonian FC | details |
| 29 January 1966 | North of Scotland Cup | Ross County 3:4 Caledonian FC | details |
| 20 November 1965 | Scottish Qualifying Cup | Caledonian FC 3:0 Ross County | details |
| 13 November 1965 | Scottish Qualifying Cup | Ross County 2:1 Caledonian FC | details |
| 12 May 1965 | Highland League | Caledonian FC 1:1 Ross County | details |
| 21 April 1965 | Highland League | Ross County 1:1 Caledonian FC | details |
| 21 October 1964 | Inverness Cup | Ross County 4:2 Caledonian FC | details |
| 14 October 1964 | Inverness Cup | Caledonian FC 2:2 Ross County | details |
| 24 August 1964 | Highland League Cup | Caledonian FC 2:3 Ross County | details |
| 12 August 1964 | Highland League Cup | Ross County 5:0 Caledonian FC | details |
| 04 January 1964 | Highland League | Caledonian FC 8:2 Ross County | details |
| 19 November 1963 | Inverness Cup | Ross County 0:1 Caledonian FC | details |
| 28 October 1963 | Highland League | Ross County 1:4 Caledonian FC | details |
| 26 August 1963 | Highland League Cup | Caledonian FC 2:5 Ross County | details |
| 14 August 1963 | Highland League Cup | Ross County 4:3 Caledonian FC | details |
| 20 May 1963 | Highland League | Caledonian FC 3:1 Ross County | details |
| 16 March 1963 | North of Scotland Cup | Caledonian FC 7:2 Ross County | details |
| 09 March 1963 | North of Scotland Cup | Ross County 0:0 Caledonian FC | details |
| 01 December 1962 | Highland League | Ross County 1:0 Caledonian FC | details |
| 25 August 1962 | Highland League Cup | Caledonian FC 3:4 Ross County | details |
| 11 August 1962 | Highland League Cup | Ross County 2:4 Caledonian FC | details |
| 11 April 1962 | North of Scotland Cup | Ross County 2:1 Caledonian FC | details |
| 05 April 1962 | Highland League Cup | Caledonian FC 2:1 Ross County | details |
| 25 November 1961 | Highland League | Caledonian FC 0:4 Ross County | details |
| 30 August 1961 | Highland League | Ross County 0:1 Caledonian FC | details |
| 31 December 1960 | Highland League | Ross County 1:1 Caledonian FC | details |
| 15 October 1960 | Highland League | Caledonian FC 2:0 Ross County | details |
| 24 August 1960 | Highland League Cup | Ross County 0:2 Caledonian FC | details |
| 13 August 1960 | Highland League Cup | Caledonian FC 5:0 Ross County | details |
| 23 January 1960 | Highland League | Caledonian FC 1:1 Ross County | details |
| 02 January 1960 | Highland League | Ross County 5:2 Caledonian FC | details |
| 10 November 1959 | Inverness Cup | Caledonian FC 1:2 Ross County | details |
| 19 August 1959 | Highland League Cup | Ross County 0:5 Caledonian FC | details |
| 15 August 1959 | Highland League | Caledonian FC 5:1 Ross County | details |
| 09 May 1959 | Highland League | Ross County 2:1 Caledonian FC | details |
| 29 November 1958 | Highland League | Caledonian FC 2:1 Ross County | details |
| 27 September 1958 | Scottish Qualifying Cup | Ross County 2:1 Caledonian FC | details |
| 20 September 1958 | Scottish Qualifying Cup | Caledonian FC 2:2 Ross County | details |
| 20 August 1958 | Highland League Cup | Ross County 3:0 Caledonian FC | details |
| 16 August 1958 | Highland League Cup | Caledonian FC 1:3 Ross County | details |
| 05 April 1958 | Highland League | Caledonian FC 1:2 Ross County | details |
| 08 March 1958 | Highland League | Ross County 4:1 Caledonian FC | details |
| 29 December 1956 | Highland League | Ross County 1:5 Caledonian FC | details |
| 22 December 1956 | Highland League | Caledonian FC 6:2 Ross County | details |
| 22 August 1956 | Highland League Cup | Ross County 0:2 Caledonian FC | details |
| 18 August 1956 | Highland League Cup | Caledonian FC 0:2 Ross County | details |
| 14 January 1956 | Highland League | Caledonian FC 3:0 Ross County | details |
| 07 January 1956 | Highland League | Ross County 1:0 Caledonian FC | details |
| 27 August 1955 | Highland League Cup | Caledonian FC 2:0 Ross County | details |
| 17 August 1955 | Highland League Cup | Ross County 2:2 Caledonian FC | details |
| 20 April 1955 | Highland League | Caledonian FC 3:1 Ross County | details |
| 04 December 1954 | Highland League | Ross County 2:4 Caledonian FC | details |
| 28 August 1954 | Highland League Cup | Caledonian FC 2:1 Ross County | details |
| 18 August 1954 | Highland League Cup | Ross County 3:1 Caledonian FC | details |
| 26 December 1953 | Highland League | Ross County 1:5 Caledonian FC | details |
| 14 November 1953 | Highland League | Caledonian FC 5:1 Ross County | details |
| 22 August 1953 | Highland League Cup | Caledonian FC 3:0 Ross County | details |
| 12 August 1953 | Highland League Cup | Ross County 3:2 Caledonian FC | details |
| 28 March 1953 | Highland League | Ross County 3:0 Caledonian FC | details |
| 14 February 1953 | North of Scotland Cup | Ross County 2:3 Caledonian FC | details |
| 27 December 1952 | Highland League | Caledonian FC 6:2 Ross County | details |
| 27 August 1952 | Highland League Cup | Caledonian FC 5:2 Ross County | details |
| 13 August 1952 | Highland League Cup | Ross County 0:4 Caledonian FC | details |
| 29 December 1951 | Highland League | Ross County 2:3 Caledonian FC | details |
| 22 December 1951 | Highland League | Caledonian FC 3:3 Ross County | details |
| 27 August 1951 | Highland League Cup | Ross County 2:2 Caledonian FC | details |
| 18 August 1951 | Highland League Cup | Caledonian FC 9:4 Ross County | details |
| 21 July 1951 | FRIENDLY | Ross County 4:4 Caledonian FC | details |
| 24 February 1951 | Highland League | Caledonian FC 1:0 Ross County | details |
| 23 December 1950 | Highland League | Ross County 2:2 Caledonian FC | details |
| 03 January 1950 | Highland League | Ross County 2:5 Caledonian FC | details |
| 22 October 1949 | Scottish Qualifying Cup | Ross County 1:3 Caledonian FC | details |
| 17 September 1949 | Highland League | Caledonian FC 4:0 Ross County | details |
| 13 April 1949 | Highland League | Ross County 5:2 Caledonian FC | details |
| 05 March 1949 | Highland League | Caledonian FC 5:2 Ross County | details |
| 19 August 1948 | Highland League Cup | Ross County 1:2 Caledonian FC | details |
| 18 August 1948 | Highland League Cup | Ross County 1:3 Caledonian FC | details |
| 14 August 1948 | Highland League Cup | Caledonian FC 1:3 Ross County | details |
| 07 April 1948 | Stuart Cup | Ross County 4:2 Caledonian FC | details |
| 31 March 1948 | Stuart Cup | Caledonian FC 4:1 Ross County | details |
| 29 November 1947 | Highland League | Ross County 4:2 Caledonian FC | details |
| 22 November 1947 | Highland League | Caledonian FC 2:4 Ross County | details |
| 11 January 1947 | Highland League | Caledonian FC 5:1 Ross County | details |
| 02 November 1946 | Highland League | Ross County 1:2 Caledonian FC | details |
| 21 August 1946 | Highland League Cup | Ross County 0:3 Caledonian FC | details |
| 17 August 1946 | Highland League Cup | Caledonian FC 1:2 Ross County | details |
| 29 December 1945 | Stuart Cup | Caledonian FC 1:0 Ross County | details |
| 15 December 1945 | Stuart Cup | Ross County 1:5 Caledonian FC | details |
| 08 December 1945 | North of Scotland League | Caledonian FC 2:1 Ross County | details |
| 15 September 1945 | North of Scotland League | Ross County 3:2 Caledonian FC | details |
| 18 November 1939 | Highland Emergency League | Ross County 4:2 Caledonian FC | details |
| 04 November 1939 | Highland Emergency League | Caledonian FC 0:3 Ross County | details |
| 18 March 1939 | Highland League | Ross County 3:7 Caledonian FC | details |
| 11 February 1939 | North of Scotland Cup | Ross County 2:3 Caledonian FC | details |
| 03 December 1938 | Highland League | Caledonian FC 4:2 Ross County | details |
| 26 February 1938 | North of Scotland Cup | Caledonian FC 3:1 Ross County | details |
| 19 February 1938 | North of Scotland Cup | Ross County 1:1 Caledonian FC | details |
| 25 September 1937 | Highland League | Caledonian FC 0:3 Ross County | details |
| 21 August 1937 | Highland League | Ross County 1:3 Caledonian FC | details |
| 19 April 1937 | Highland League | Caledonian FC 3:3 Ross County | details |
| 19 September 1936 | Highland League | Ross County 3:0 Caledonian FC | details |
| 26 August 1936 | Inverness Cup | Caledonian FC 0:2 Ross County | details |
| 12 August 1936 | Inverness Cup | Ross County 1:2 Caledonian FC | details |
| 25 April 1936 | Highland League | Caledonian FC 1:0 Ross County | details |
| 23 April 1936 | Stuart Cup | Ross County 3:0 Caledonian FC | details |
| 30 November 1935 | Highland League | Caledonian FC 4:1 Ross County | details |
| 05 October 1935 | Scottish Qualifying Cup | Caledonian FC 1:2 Ross County | details |
| 17 August 1935 | Highland League | Ross County 1:5 Caledonian FC | details |
| 15 August 1935 | Inverness Cup | Caledonian FC 5:1 Ross County | details |
| 12 August 1935 | Inverness Cup | Ross County 4:2 Caledonian FC | details |
| 15 December 1934 | Highland League | Caledonian FC 6:3 Ross County | details |
| 24 November 1934 | Highland League | Ross County 1:3 Caledonian FC | details |
| 13 January 1934 | Highland League | Ross County 4:2 Caledonian FC | details |
| 28 October 1933 | Highland League | Caledonian FC 1:5 Ross County | details |
| 14 January 1933 | Highland League | Caledonian FC 1:0 Ross County | details |
| 13 August 1932 | Highland League | Ross County 4:2 Caledonian FC | details |
| 14 April 1932 | Inverness Cup | Caledonian FC 2:1 Ross County | details |
| 02 April 1932 | Inverness Cup | Ross County 0:0 Caledonian FC | details |
| 05 December 1931 | Highland League | Caledonian FC 3:1 Ross County | details |
| 21 November 1931 | Highland League | Ross County 1:1 Caledonian FC | details |
| 02 May 1931 | Inverness Charity Cup | Caledonian FC 3:1 Ross County | details |
| 23 April 1931 | Inverness Cup | Caledonian FC 2:1 Ross County | details |
| 15 April 1931 | Inverness Cup | Ross County 2:0 Caledonian FC | details |
| 24 January 1931 | Highland League | Caledonian FC 2:1 Ross County | details |
| 13 December 1930 | Highland League | Ross County 2:0 Caledonian FC | details |
| 20 September 1930 | Scottish Qualifying Cup | Ross County 1:2 Caledonian FC | details |
| 13 September 1930 | Scottish Qualifying Cup | Caledonian FC 3:3 Ross County | details |
| 22 February 1930 | North of Scotland Cup | Caledonian FC 1:3 Ross County | details |
| 01 February 1930 | FRIENDLY | Ross County 2:1 Caledonian FC | details |
| 14 September 1929 | Highland League | Caledonian FC 1:1 Ross County | details |
| 17 August 1929 | Highland League | Ross County 2:1 Caledonian FC | details |