SCOTTISH HIGHLAND LEAGUE CUP WINNERS BY DATE
| Forres Mechanics |
1946-47 |
| Clachnacuddin |
1947-48 |
| Huntly |
1948-49 |
| Ross County |
1949-50 |
| Clachnacuddin |
1950-51 |
| Huntly |
1951-52 |
| Caledonian |
1952-53 |
| Buckie Thistle |
1953-54 |
| Forres Mechanics |
1954-55 |
| Buckie Thistle |
1955-56 1956-57 1957-58 |
| Fraserburgh |
1958-59 |
| Elgin City |
1959-60 |
| Buckie Thistle |
1960-61 |
| Lossiemouth |
1961-62 |
| Peterhead |
1962-63 |
| Nairn County |
1963-64 |
| Keith |
1964-65 |
| Peterhead |
1965-66 |
| Elgin City |
1966-67 |
| Peterhead |
1967-68 |
| Ross County |
1968-69 |
| Caledonian |
1969-70 |
| Inverness Thistle |
1970-71 |
| Caledonian |
1971-72 |
| Inverness Thistle |
1972-73 |
| Keith |
1973-74 1974-75 1975-76 |
| Caledonian |
1976-77 1977-78 |
| Ross County |
1978-79 |
| Buckie Thistle |
1979-80 |
| Peterhead |
1980-81 |
| Clachnacuddin |
1981-82 |
| Elgin City |
1982-83 |
| Keith |
1983-84 |
| Forres Mechanics |
1984-85 |
| Keith |
1985-86 |
| Buckie Thistle |
1986-87 |
| Inverness Thistle |
1987-88 |
| Keith |
1988-89 |
| Peterhead |
1989-90 |
| Elgin City |
1990-91 |
| Ross County |
1991-92 |
| Huntly |
1992-93 1993-94 |
| Cove Rangers |
1994-95 |
| Huntly |
1995-96 |
| Lossiemouth |
1996-97 |
| Elgin City |
1997-98 |
| Forres Mechanics |
1998-99 |
| Cove Rangers |
1999-00 |
| Forres Mechanics |
2000-01 2001-02 |
| Keith |
2002-03 |
| Clachnacuddin |
2003-04 |
| Cove Rangers |
2004-05 |
| Fraserburgh |
2005-06 |
| Keith |
2006-07 |
| Inverurie Loco Works |
2007-08 2008-09 |
| Forres Mechanics |
2009-10 |
| Nairn County |
2010-11 |
| Buckie Thistle |
2011-12 |
| Keith |
2012-13 |
| Clachnacuddin |
2013-14 |
| Cove Rangers |
2014-15 |
| Brora Rangers |
2015-16 |
| Cove Rangers |
2016-17 |
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Last Updated 09/08/2010