Scottish League Cup 2023/24, Group A |
 | 15.07.2023 | | Stirling Albion | – | Ayr United | | 1:1 (1:0),
pen. 3:4 |
| Stirling |
Scottish League Cup 2022/23, Group F |
| 19.07.2022 | | Annan Athletic | – | Ayr United | | 1:1 (0:0),
pen. 5:4 |
| Annan |
Scottish League Cup 2021/22, Second round |
| 14.08.2021 | | Ayr United | – | Dundee United | | 1:1 aet
(0:0, 1:1),
pen. 3:4 |
| Ayr |
Scottish League Cup 2021/22, Group E |
| 10.07.2021 | | Albion Rovers | – | Ayr United | | 0:0,
pen. 4:2 |
| Coatbridge |
Scottish League Cup 2020/21, Group F |
| 14.11.2020 | | Ayr United | – | Stranraer | | 1:1 (0:1),
pen. 6:5 |
| Ayr |
Scottish League Cup 2019/20, Group G |
| 27.07.2019 | | Ayr United | – | Stranraer | | 2:2 (2:1),
pen. 5:6 |
| Ayr |
Scottish League Cup 2011/12, Third Round |
| 21.09.2011 | | Ayr United | – | Hearts | | 1:1 aet
(0:0, 1:1),
pen. 4:1 |
| Ayr |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Stirling Albion | – | Ayr United | | 1:1 aet
(1:0, 1:1) |
| Stirling |
Scottish League Cup 2006/07, Second Round |
| 22.08.2006 | | Ayr United | – | Dunfermline Athletic | | 0:0 aet,
pen. 6:7 |
| Ayr |
Scottish League Cup 2001/02, Third Round |
| 09.10.2001 | | Ayr United | – | Kilmarnock | | 0:0 aet,
pen. 5:4 |
| |
Scottish League Cup 2000/01, First Round |
| 09.08.2000 | | Dumbarton | – | Ayr United | | 0:0 aet,
pen. 5:4 |
| |
Scottish League Cup 1997, Second Round |
| 09.08.1997 | | Dunfermline Athletic | – | Ayr United | | 0:0 aet,
pen. ?:? |
| |
Scottish League Cup 1982, Group 6 |
| 25.08.1982 | | Stirling Albion | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1982, Group 6 |
| 18.08.1982 | | Ayr United | – | Stirling Albion | | 0:0 |
| |
Scottish League Cup 1980, Semifinal |
| 05.11.1980 | | Ayr United | – | Dundee | | 1:1 |
| |
Scottish League Cup 1980, Quarterfinal |
| 08.10.1980 | | Ayr United | – | Hibernian | | 2:2 |
| |
Scottish League Cup 1979, Second Round |
| 01.09.1979 | | Ayr United | – | Hearts | | 2:2 |
| |
Scottish League Cup 1978/79, Quarterfinal |
| 08.11.1978 | | Ayr United | – | Aberdeen | | 3:3 |
| |
Scottish League Cup 1978/79, Third Round |
| 11.10.1978 | | Ayr United | – | Falkirk | | 1:1 |
| |
Scottish League Cup 1976, Group 2 |
| 01.09.1976 | | St. Mirren | – | Ayr United | | 2:2 |
| |
Scottish League Cup 1976, Group 2 |
| 28.08.1976 | | Ayr United | – | Aberdeen | | 1:1 |
| |
Scottish League Cup 1975, Group 2 |
| 27.08.1975 | | Ayr United | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1975, Group 2 |
| 16.08.1975 | | Ayr United | – | Dundee | | 1:1 |
| |
Scottish League Cup 1975, Group 2 |
| 09.08.1975 | | Dunfermline Athletic | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1974, Group 4 |
| 28.08.1974 | | Ayr United | – | Dundee United | | 2:2 |
| |
Scottish League Cup 1972, Supplementary Round |
| 04.09.1972 | | Alloa Athletic | – | Ayr United | | 0:0 |
| |
Scottish League Cup 1971, Group 4 |
| 14.08.1971 | | Ayr United | – | Morton | | 1:1 |
| |
Scottish League Cup 1970, Group 3 |
| 22.08.1970 | | Ayr United | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1970, Group 3 |
| 15.08.1970 | | Ayr United | – | St. Mirren | | 2:2 |
| |
Scottish League Cup 1969, Semifinal |
| 08.10.1969 | | Celtic | – | Ayr United | | 3:3 |
| |
Scottish League Cup 1969, Group 6 |
| 20.08.1969 | | Ayr United | – | East Stirlingshire | | 0:0 |
| |
Scottish League Cup 1968/69, Group 5 |
| 17.08.1968 | | Arbroath | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1966, Quarterfinal |
| 14.09.1966 | | Ayr United | – | Rangers | | 1:1 |
| |
Scottish League Cup 1966, Group 5 |
| 20.08.1966 | | Ayr United | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1966, Group 5 |
| 17.08.1966 | | Ayr United | – | Raith Rovers | | 0:0 |
| |
Scottish League Cup 1966, Group 5 |
| 13.08.1966 | | Berwick Rangers | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1965, Quarterfinal |
| 22.09.1965 | | Ayr United | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1964, Group 8 |
| 26.08.1964 | | Morton | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1962, Group 5 |
| 29.08.1962 | | Berwick Rangers | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1962, Group 5 |
| 18.08.1962 | | Hamilton Academical | – | Ayr United | | 4:4 |
| |
Scottish League Cup 1962, Group 5 |
| 15.08.1962 | | Ayr United | – | Berwick Rangers | | 2:2 |
| |
Scottish League Cup 1961, Group 8 |
| 02.09.1961 | | Falkirk | – | Ayr United | | 4:4 |
| |
Scottish League Cup 1961, Group 8 |
| 19.08.1961 | | Ayr United | – | Falkirk | | 1:1 |
| |
Scottish League Cup 1960, Group 4 |
| 27.08.1960 | | Ayr United | – | Aberdeen | | 1:1 |
| |
Scottish League Cup 1960, Group 4 |
| 20.08.1960 | | Raith Rovers | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1959, Group 5 |
| 26.08.1959 | | Falkirk | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1959, Group 5 |
| 22.08.1959 | | Ayr United | – | Berwick Rangers | | 1:1 |
| |
Scottish League Cup 1958, Group 8 |
| 30.08.1958 | | Forfar Athletic | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1957, Group 6 |
| 17.08.1957 | | Cowdenbeath | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1956, Group 8 |
| 25.08.1956 | | Ayr United | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1956, Group 8 |
| 18.08.1956 | | Stenhousemuir | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1956, Group 8 |
| 15.08.1956 | | Ayr United | – | Third Lanark | | 3:3 |
| |
Scottish League Cup 1955, Group 6 |
| 03.09.1955 | | Ayr United | – | Stirling Albion | | 2:2 |
| |
Scottish League Cup 1954, Group 6 |
| 18.08.1954 | | Ayr United | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1953, Group 6 |
| 15.08.1953 | | Queen's Park | – | Ayr United | | 0:0 |
| |
Scottish League Cup 1952, Group 6 |
| 27.08.1952 | | Dumbarton | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1950, Group 5 |
| 16.08.1950 | | Ayr United | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1949, Group 7 |
| 27.08.1949 | | Morton | – | Ayr United | | 3:3 |
| |
Scottish League Cup 1949, Group 7 |
| 20.08.1949 | | Ayr United | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1949, Group 7 |
| 17.08.1949 | | Alloa Athletic | – | Ayr United | | 2:2 |
| |
Scottish League Cup 1948, Group 8 |
| 02.10.1948 | | Arbroath | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1947, Group 8 |
| 09.08.1947 | | Ayr United | – | Kilmarnock | | 2:2 |
| |
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