Scottish League Cup 2023/24, Second Round |
| 19.08.2023 | | Livingston | | Ayr United | | 2:0 (1:0) |
| Livingston |
Scottish League Cup 2022/23, Group F |
| 23.07.2022 | | St. Johnstone | | Ayr United | | 1:0 (1:0) |
| Perth |
Scottish League Cup 2022/23, Group F |
| 12.07.2022 | | Ayr United | | Queen of the South | | 0:3 (0:1) |
| Ayr |
Scottish League Cup 2020/21, Second round |
| 28.11.2020 | | Livingston | | Ayr United | | 4:0 (4:0) |
| Livingston |
Scottish League Cup 2020/21, Group F |
| 10.10.2020 | | Hamilton Academical | | Ayr United | | 2:1 (2:0) |
| Hamilton |
Scottish League Cup 2019/20, Group G |
| 16.07.2019 | | Livingston | | Ayr United | | 2:1 (1:0) |
| Livingston |
Scottish League Cup 2018/19, Quarterfinal |
| 26.09.2018 | | Rangers | | Ayr United | | 4:0 (2:0) |
| Glasgow |
Scottish League Cup 2017/18, Second round |
| 08.08.2017 | | Hibernian | | Ayr United | | 5:0 (2:0) |
| Edinburgh |
Scottish League Cup 2016/17, Second round |
| 10.08.2016 | | Ayr United | | Aberdeen | | 1:2 (1:2) |
| Ayr |
Scottish League Cup 2016/17, First Round, Group G |
| 19.07.2016 | | St. Mirren | | Ayr United | | 1:0 (0:0) |
| Paisley |
Scottish League Cup 2015/16, Second Round |
| 25.08.2015 | | Ross County | | Ayr United | | 2:0 (1:0) |
| Dingwall |
Scottish League Cup 2014/15, Second Round |
| 26.08.2014 | | Kilmarnock | | Ayr United | | 1:0 (0:0) |
| Kilmarnock |
Scottish League Cup 2013/14, First Round |
| 06.08.2013 | | Partick Thistle | | Ayr United | | 2:1 (1:0) |
| Glasgow |
Scottish League Cup 2012/13, Second Round |
| 29.08.2012 | | St. Mirren | | Ayr United | | 5:1 (4:1) |
| Paisley |
Scottish League Cup 2011/12, Semifinal |
| 28.01.2012 | | Ayr United | | Kilmarnock | | 0:1 aet (0:0) |
| Glasgow |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Elgin City | | Ayr United | | 3:2 aet (1:1, 2:2) |
| Elgin |
Scottish League Cup 2009/10, Second Round |
| 26.08.2009 | | Ayr United | | St. Mirren | | 0:2 (0:1) |
| Ayr |
Scottish League Cup 2008/09, Second Round |
| 27.08.2008 | | Ayr United | | Aberdeen | | 0:1 (0:1) |
| Ayr |
Scottish League Cup 2007/08, First Round |
| 07.08.2007 | | Livingston | | Ayr United | | 5:0 (3:0) |
| Livingston |
Scottish League Cup 2005/06, Third Round |
| 21.09.2005 | | Ayr United | | Hibernian | | 1:2 (0:2) |
| |
Scottish League Cup 2004/05, First Round |
| 17.08.2004 | | Hamilton Academical | | Ayr United | | 4:1 (2:0) |
| |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | Ayr United | | Dumbarton | | 1:2 (0:1) |
| |
Scottish League Cup 2002/03, Second Round |
| 24.09.2002 | | Ayr United | | Falkirk | | 0:2 (0:1) |
| |
Scottish League Cup 2001/02, Final |
| 17.03.2002 | | Ayr United | | Rangers | | 0:4 (0:1) |
| Glasgow |
Scottish League Cup 1999/00, Third Round |
| 13.10.1999 | | Ayr United | | Celtic | | 0:4 |
| |
Scottish League Cup 1998, Quarterfinal |
| 08.09.1998 | | Ayr United | | Rangers | | 0:2 |
| |
Scottish League Cup 1996, Third Round |
| 04.09.1996 | | Rangers | | Ayr United | | 3:1 |
| |
Scottish League Cup 1995, Second Round |
| 19.08.1995 | | Ayr United | | Celtic | | 0:3 |
| |
Scottish League Cup 1994, Second Round |
| 17.08.1994 | | Ayr United | | Celtic | | 0:3 |
| |
Scottish League Cup 1994, Second Round |
| 16.08.1994 | | Ayr United | | Celtic | | 0:1 |
| |
Scottish League Cup 1993, Second Round |
| 10.08.1993 | | Ayr United | | Motherwell | | 0:6 |
| |
Scottish League Cup 1992, Second Round |
| 11.08.1992 | | Partick Thistle | | Ayr United | | 2:0 |
| |
Scottish League Cup 1991, Quarterfinal |
| 03.09.1991 | | Ayr United | | Hibernian | | 0:2 |
| |
Scottish League Cup 1990, Second Round |
| 22.08.1990 | | Celtic | | Ayr United | | 4:0 |
| |
Scottish League Cup 1989, Second Round |
| 15.08.1989 | | Ayr United | | Hamilton Academical | | 0:1 |
| |
Scottish League Cup 1988, Second Round |
| 17.08.1988 | | Celtic | | Ayr United | | 4:1 |
| |
Scottish League Cup 1987, Second Round |
| 19.08.1987 | | Ayr United | | Dumbarton | | 0:1 |
| |
Scottish League Cup 1986, Third Round |
| 27.08.1986 | | Ayr United | | Dundee United | | 0:3 |
| |
Scottish League Cup 1985, Second Round |
| 21.08.1985 | | Aberdeen | | Ayr United | | 5:0 |
| |
Scottish League Cup 1984, Third Round |
| 29.08.1984 | | Hearts | | Ayr United | | 1:0 |
| |
Scottish League Cup 1983/84, Second Round |
| 27.08.1983 | | Clydebank | | Ayr United | | 1:0 |
| |
Scottish League Cup 1983/84, Second Round |
| 23.08.1983 | | Ayr United | | Clydebank | | 1:2 |
| |
Scottish League Cup 1982, Group 6 |
| 21.08.1982 | | Ayr United | | Queen of the South | | 0:2 |
| |
Scottish League Cup 1982, Group 6 |
| 14.08.1982 | | St. Mirren | | Ayr United | | 3:1 |
| |
Scottish League Cup 1981, Group 4 |
| 22.08.1981 | | Dundee United | | Ayr United | | 2:1 |
| |
Scottish League Cup 1981, Group 4 |
| 08.08.1981 | | Ayr United | | Dundee United | | 3:4 |
| |
Scottish League Cup 1980, Semifinal |
| 19.11.1980 | | Dundee | | Ayr United | | 3:2 |
| |
Scottish League Cup 1980, First Round |
| 13.08.1980 | | Ayr United | | Morton | | 1:2 |
| |
Scottish League Cup 1979, Third Round |
| 10.10.1979 | | Ayr United | | Dundee | | 0:1 |
| |
Scottish League Cup 1979, Third Round |
| 26.09.1979 | | Dundee | | Ayr United | | 2:1 |
| |
Scottish League Cup 1978/79, Quarterfinal |
| 15.11.1978 | | Aberdeen | | Ayr United | | 3:1 |
| |
Scottish League Cup 1977/78, Third Round |
| 26.10.1977 | | Forfar Athletic | | Ayr United | | 3:1 |
| |
Scottish League Cup 1977/78, Second Round |
| 03.09.1977 | | Queen's Park | | Ayr United | | 1:0 aet, pen. 2:4 |
| |
Scottish League Cup 1976, Group 2 |
| 21.08.1976 | | Aberdeen | | Ayr United | | 1:0 |
| |
Scottish League Cup 1976, Group 2 |
| 18.08.1976 | | Kilmarnock | | Ayr United | | 2:0 |
| |
Scottish League Cup 1975, Group 2 |
| 20.08.1975 | | Hibernian | | Ayr United | | 2:1 |
| |
Scottish League Cup 1974, Group 4 |
| 24.08.1974 | | Motherwell | | Ayr United | | 5:0 |
| |
Scottish League Cup 1974, Group 4 |
| 21.08.1974 | | Celtic | | Ayr United | | 5:2 |
| |
Scottish League Cup 1974, Group 4 |
| 17.08.1974 | | Ayr United | | Motherwell | | 0:3 |
| |
Scottish League Cup 1974, Group 4 |
| 10.08.1974 | | Dundee United | | Ayr United | | 3:1 |
| |
Scottish League Cup 1973, Group 2 |
| 29.08.1973 | | Dumbarton | | Ayr United | | 1:0 |
| |
Scottish League Cup 1973, Group 2 |
| 22.08.1973 | | Ayr United | | Hibernian | | 0:2 |
| |
Scottish League Cup 1973, Group 2 |
| 18.08.1973 | | Morton | | Ayr United | | 3:2 |
| |
Scottish League Cup 1973, Group 2 |
| 15.08.1973 | | Hibernian | | Ayr United | | 1:0 |
| |
Scottish League Cup 1972, Supplementary Round |
| 06.09.1972 | | Ayr United | | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1972, Group 3 |
| 30.08.1972 | | Ayr United | | Rangers | | 1:2 |
| |
Scottish League Cup 1972, Group 3 |
| 19.08.1972 | | Rangers | | Ayr United | | 2:1 |
| |
Scottish League Cup 1972, Group 3 |
| 16.08.1972 | | Clydebank | | Ayr United | | 1:0 |
| |
Scottish League Cup 1971, Group 4 |
| 01.09.1971 | | Celtic | | Ayr United | | 4:1 |
| |
Scottish League Cup 1971, Group 4 |
| 28.08.1971 | | Morton | | Ayr United | | 2:0 |
| |
Scottish League Cup 1971, Group 4 |
| 25.08.1971 | | Ayr United | | Rangers | | 0:4 |
| |
Scottish League Cup 1971, Group 4 |
| 21.08.1971 | | Ayr United | | Celtic | | 0:3 |
| |
Scottish League Cup 1971, Group 4 |
| 18.08.1971 | | Rangers | | Ayr United | | 4:0 |
| |
Scottish League Cup 1970, Group 3 |
| 19.08.1970 | | Dundee | | Ayr United | | 4:1 |
| |
Scottish League Cup 1970, Group 3 |
| 12.08.1970 | | Ayr United | | Dundee | | 1:2 |
| |
Scottish League Cup 1970, Group 3 |
| 08.08.1970 | | Kilmarnock | | Ayr United | | 1:0 |
| |
Scottish League Cup 1969, Semifinal |
| 13.10.1969 | | Celtic | | Ayr United | | 2:1 |
| |
Scottish League Cup 1969, Group 6 |
| 27.08.1969 | | Queen of the South | | Ayr United | | 2:1 |
| |
Scottish League Cup 1968/69, Quarterfinal |
| 11.09.1968 | | Ayr United | | Clyde | | 0:1 |
| |
Scottish League Cup 1967, Quarterfinal |
| 27.09.1967 | | Ayr United | | Celtic | | 0:2 |
| |
Scottish League Cup 1967, Quarterfinal |
| 13.09.1967 | | Celtic | | Ayr United | | 6:2 |
| |
Scottish League Cup 1967, Group 5 |
| 19.08.1967 | | Berwick Rangers | | Ayr United | | 2:1 |
| |
Scottish League Cup 1966, Quarterfinal |
| 21.09.1966 | | Rangers | | Ayr United | | 3:0 |
| |
Scottish League Cup 1966, Group 5 |
| 31.08.1966 | | Raith Rovers | | Ayr United | | 3:1 |
| |
Scottish League Cup 1965, Quarterfinal |
| 15.09.1965 | | Kilmarnock | | Ayr United | | 2:0 |
| |
Scottish League Cup 1964, Group 8 |
| 29.08.1964 | | Dumbarton | | Ayr United | | 2:1 |
| |
Scottish League Cup 1964, Group 8 |
| 12.08.1964 | | Ayr United | | Morton | | 0:1 |
| |
Scottish League Cup 1964, Group 8 |
| 08.08.1964 | | Berwick Rangers | | Ayr United | | 3:1 |
| |
Scottish League Cup 1963, Group 6 |
| 31.08.1963 | | Ayr United | | Stranraer | | 1:2 |
| |
Scottish League Cup 1963, Group 6 |
| 28.08.1963 | | Ayr United | | Clyde | | 2:4 |
| |
Scottish League Cup 1963, Group 6 |
| 24.08.1963 | | Morton | | Ayr United | | 5:2 |
| |
Scottish League Cup 1963, Group 6 |
| 17.08.1963 | | Stranraer | | Ayr United | | 2:1 |
| |
Scottish League Cup 1963, Group 6 |
| 10.08.1963 | | Ayr United | | Morton | | 0:1 |
| |
Scottish League Cup 1962, Group 5 |
| 11.08.1962 | | East Stirlingshire | | Ayr United | | 4:1 |
| |
Scottish League Cup 1961, Quarterfinal |
| 20.09.1961 | | Stirling Albion | | Ayr United | | 3:0 aet |
| |
Scottish League Cup 1960, Group 4 |
| 03.09.1960 | | Ayr United | | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1960, Group 4 |
| 31.08.1960 | | Dundee | | Ayr United | | 3:0 |
| |
Scottish League Cup 1960, Group 4 |
| 17.08.1960 | | Ayr United | | Dundee | | 1:2 |
| |
Scottish League Cup 1960, Group 4 |
| 13.08.1960 | | Aberdeen | | Ayr United | | 4:3 |
| |
Scottish League Cup 1959, Group 5 |
| 15.08.1959 | | Hamilton Academical | | Ayr United | | 1:0 |
| |
Scottish League Cup 1958, Quarterfinal |
| 17.09.1958 | | Hearts | | Ayr United | | 3:1 |
| |
Scottish League Cup 1958, Quarterfinal |
| 10.09.1958 | | Ayr United | | Hearts | | 1:5 |
| |
Scottish League Cup 1958, Group 8 |
| 09.08.1958 | | Hamilton Academical | | Ayr United | | 3:1 |
| |
Scottish League Cup 1957, Group 6 |
| 28.08.1957 | | Dunfermline Athletic | | Ayr United | | 3:0 |
| |
Scottish League Cup 1957, Group 6 |
| 10.08.1957 | | Brechin City | | Ayr United | | 5:2 |
| |
Scottish League Cup 1956, Group 8 |
| 11.08.1956 | | Dundee United | | Ayr United | | 6:1 |
| |
Scottish League Cup 1955, Group 6 |
| 31.08.1955 | | Queen's Park | | Ayr United | | 2:0 |
| |
Scottish League Cup 1955, Group 6 |
| 20.08.1955 | | Stirling Albion | | Ayr United | | 3:1 |
| |
Scottish League Cup 1955, Group 6 |
| 13.08.1955 | | St. Johnstone | | Ayr United | | 5:1 |
| |
Scottish League Cup 1954, Quarterfinal |
| 25.09.1954 | | Airdrieonians | | Ayr United | | 6:1 |
| |
Scottish League Cup 1954, Group 6 |
| 21.08.1954 | | Dunfermline Athletic | | Ayr United | | 4:0 |
| |
Scottish League Cup 1953, Quarterfinal |
| 12.09.1953 | | Rangers | | Ayr United | | 4:2 |
| |
Scottish League Cup 1953, Group 6 |
| 22.08.1953 | | Stenhousemuir | | Ayr United | | 4:2 |
| |
Scottish League Cup 1952, Group 6 |
| 30.08.1952 | | Dundee United | | Ayr United | | 2:1 |
| |
Scottish League Cup 1952, Group 6 |
| 23.08.1952 | | Ayr United | | Stirling Albion | | 1:2 |
| |
Scottish League Cup 1952, Group 6 |
| 09.08.1952 | | Stirling Albion | | Ayr United | | 2:0 |
| |
Scottish League Cup 1951, Group 8 |
| 01.09.1951 | | Forfar Athletic | | Ayr United | | 3:0 |
| |
Scottish League Cup 1951, Group 8 |
| 25.08.1951 | | Ayr United | | Kilmarnock | | 1:2 |
| |
Scottish League Cup 1951, Group 8 |
| 18.08.1951 | | Ayr United | | Forfar Athletic | | 2:3 |
| |
Scottish League Cup 1951, Group 8 |
| 11.08.1951 | | Kilmarnock | | Ayr United | | 3:0 |
| |
Scottish League Cup 1950, Semifinal |
| 07.10.1950 | | Motherwell | | Ayr United | | 4:3 |
| |
Scottish League Cup 1949, Group 7 |
| 03.09.1949 | | Cowdenbeath | | Ayr United | | 2:0 |
| |
Scottish League Cup 1949, Group 7 |
| 13.08.1949 | | Ayr United | | Morton | | 3:4 |
| |
Scottish League Cup 1948, Group 8 |
| 16.10.1948 | | Ayr United | | Airdrieonians | | 1:4 |
| |
Scottish League Cup 1948, Group 8 |
| 25.09.1948 | | Airdrieonians | | Ayr United | | 6:1 |
| |
Scottish League Cup 1947, Group 8 |
| 13.09.1947 | | East Fife | | Ayr United | | 5:0 |
| |
Scottish League Cup 1947, Group 8 |
| 23.08.1947 | | Ayr United | | East Fife | | 2:5 |
| |
Scottish League Cup 1946/47, Section 8 |
| 26.10.1946 | | Airdrieonians | | Ayr United | | 3:0 |
| |
Scottish League Cup 1946/47, Section 8 |
| 21.09.1946 | | Albion Rovers | | Ayr United | | 5:4 |
| |