LIST OF LEAGUE CUP WINNERS
| SEASON | LEAGUE CUP WINNERS | SCORE | RUNNERS UP | VENUE | |
| 1959-60 | NANPEAN ROVERS | 3-2 | PORTHLEVEN | HELSTON | |
| 1960-61 | NANPEAN ROVERS | 4-1 | FALMOUTH TOWN RESERVES | NEWQUAY | |
| 1961-62 | FALMOUTH DOCKS | 3-2 | PORTHLEVEN | FALMOUTH TOWN | |
| 1962-63 | PORTHLEVEN | 1-1 | FALMOUTH DOCKS | FALMOUTH TOWN | |
|
REPLAY |
|||||
| PORTHLEVEN | 1-0 | FALMOUTH DOCKS | HELSTON | ||
| 1963-64 | ST BREWARD | 3-0 | RNAS CULDROSE | FALMOUTH | |
| 1964-65 | PORTHLEVEN | 2-0 | ST JUST | PENZANCE | |
| 1965-66 | PORTHLEVEN | 10-1 | ST JUST | PENZANCE | |
| 1966-67 | TRURO CITY RESERVES | 3-1 | ST BREWARD | FALMOUTH | |
| 1967-68 | ST JUST | 3-1 | TRURO CITY RESERVES | HELSTON | |
| 1968-69 | TRURO CITY RESERVES | 2-1 | ST BREWARD | FALMOUTH | |
| 1969-70 | PENZANCE RESERVES | 2-1 | ST BREWARD | TRURO | |
| 1970-71 | ST JUST | 3-1 | ILLOGAN RBL | PENZANCE | |
| 1971-72 | MARAZION BLUES | 2-1 | NEWQUAY RESERVES | TRURO | |
| 1972-73 | NEWQUAY RESERVES | 0-0 | STICKER | ILLOGAN | |
|
REPLAY |
|||||
| STICKER | 3-2 | NEWQUAY RESERVES | TRURO | ||
| 1973-74 | ILLOGAN RBL | 3-0 | ST JUST | PENZANCE | |
| 1974-75 | ST JUST | 1-0 | HELSTON ATHLETIC | PENZANCE | |
| 1975-76 | MOUSEHOLE | 1-0 | ILLOGAN RBL RESERVES | PENZANCE | |
| 1976-77 | PERRANWELL | 2-1 | RNAS CULDROSE | PENZANCE | |
| 1977-78 | TRURO CITY | 1-0 | RNAS CULDROSE | PENZANCE | |
| 1978-79 | MARAZION BLUES | 3-1 | PERRANWELL | TRURO | |
| 1979-80 | RNAS CULDROSE | 4-2 | ST DENNIS | TRURO | |
| 1980-81 | ST JUST | 2-0 | RNAS CULDROSE | PENZANCE | |
| 1981-82 | RNAS CULDROSE | 2-0 | PENZANCE RESERVES | ST JUST | |
| 1982-83 | LUDGVAN | 2-1 | MULLION | PENZANCE | |
| 1983-84 | PORTHLEVEN | 3-1 | PENRYN ATHLETIC | TRURO | |
| 1984-85 | MOUSEHOLE | 1-1 | PORTHLEVEN | PENZANCE | |
|
REPLAY |
|||||
| PORTHLEVEN | 2-1 | MOUSEHOLE | PENZANCE | ||
| 1985-86 | TRURO CITY RESERVES | 1-0 | PORTHLEVEN | PENZANCE | |
| 1986-87 | PORTHLEVEN | 3-0 | MOUSEHOLE | PENZANCE | |
| 1987-88 | PENRYN ATHLETIC | 2-2 | TRURO CITY RESERVES | PENZANCE | |
|
REPLAY |
|||||
| TRURO CITY RESERVES | 2-1 | PENRYN ATHLETIC | FALMOUTH | ||
| 1988-89 | PENRYN ATHLETIC | 2-1 | MULLION | FALMOUTH | |
| 1989-90 | PENRYN ATHLETIC | 3-0 | RNAS CULDROSE | TRURO | |
| 1990-91 | MULLION | 2-1 | PENRYN ATHLETIC | PORTHLEVEN | |
| 1991-92 | MULLION | 4-1 | ST AGNES | FALMOUTH | |
| 1992-93 | PERRANWELL | 3-0 | RNAS CULDROSE | FALMOUTH | |
| 1993-94 | PERRANWELL | 7-0 | PORTHLEVEN RESERVES | FALMOUTH | |
| 1994-95 | NEWQUAY RESERVES | 1-0 | PENRYN ATHLETIC | PORTHLEVEN | |
| 1995-96 | PENRYN ATHLETIC | 2-0 | PORTHLEVEN RESERVES | ILLOGAN | |
| 1996-97 | FALMOUTH TOWN RESERVES | 3-0 | PERRANWELL | PENZANCE | |
| 1997-98 | PERRANWELL | 2-0 | TRURO CITY RESERVES | PENRYN | |
| 1998-99 | TRURO CITY RESERVES | 2-1 | PENRYN ATHLETIC | PORTHLEVEN | |
| 1999-00 | TRURO CITY RESERVES | 1-0 | PENRYN ATHLETIC | PENZANCE | |
| 2000-01 | TRURO CITY RESERVES | 3-0 | HELSTON ATHLETIC | PORTHLEVEN | |
| 2001-02 | ST IVES TOWN | 3-1 | ILLOGAN RBL | PORTHLEVEN | |
| 2002-03 | NEWQUAY RESERVES | 3-2 | HELSTON ATHLETIC | PORTHLEVEN | |
| 2003-04 | ST JUST |
1-1 (5-4 pens) |
FALMOUTH TOWN RESERVES | PORTHLEVEN | |
| 2004-05 | ST JUST | 4-1 | FALMOUTH TOWN RESERVES | PORTHLEVEN | |
| 2005-06 | TRURO CITY RESERVES | 2-0 | ILLOGAN RBL | HELSTON | |
| 3006-07 | PENRYN ATHLETIC RESERVES |
1-1 (4-3 pens) |
MOUSEHOLE | ILLOGAN | |
| 2007-08 | TRURO CITY RESERVES | 4-1 | HELSTON ATHLETIC | PORTHLEVEN | ATTENDANCE |
| 2008-09 | PERRANPORTH | 3-0 | PERRANWELL | ST DAY | 370 |
| 2009-10 | ILLOGAN RBL | 3-0 | ST AGNES | HELSTON | 250 |
| 2010-11 | PERRANWELL |
0-0 (3-1 pens) |
PENDEEN ROVERS | PORTHLEVEN | 400 |
| 2011-12 | FALMOUTH TOWN RESERVES | 2-0 | ST JUST | ILLOGAN | 175 |
| 2012-13 | ST DAY | 2-1 | ILLOGAN RBL | PORTHLEVEN | 268 |
| 2013-14 | ST DAY | 3-2 | MULLION | PORTHLEVEN | 205 |
| 2014-15 | WENDRON UNITED |
3-3 (3-2 pens) |
LUDGVAN | HELSTON | 427 |
| 2015-16 | CARHARRACK | 3-2 | ST AGNES | PORTHLEVEN | 263 |
| 2016-17 | ST IVES TOWN | 2-1 | LUDGVAN | HAYLE | 323 |
| 2017-18 | ST DAY | 4-2 | PERRANPORTH | PORTHLEVEN | 289 |
| 2018-19 | ILLOGAN RBL | 2-1 | ST DAY | PORTHLEVEN | 421 |
| 2019-20 | NOT PLAYED DUE TO COVID | ||||
| 2020-21 | NOT PLAYED DUE TO COVID | ||||
| 2021-22 | HELSTON ATHLETIC THIRDS | 1-0 | PENRYN ATHLETIC RESERVES | WENDRON | 216 |