The Leeward Islands Football Association (LIFA) was formed in 1949.
Of the early tournaments only the winners are known; for the recent ones, the structure is largely unknown. It is also not known whether tournaments were staged in the missing years, though this is likely.
Finally, it is not always clear whether teams represent single islands or states (e.g. Saint Kitts/Nevis or Saint Christopher, Antigua/Barbuda or Antigua, etc.).
| Year | Host | Final | |||
|---|---|---|---|---|---|
| Gold Medal | Score | Silver Medal | |||
| 1949 | Antigua | ||||
| 1950 | Saint Kitts and Nevis | ||||
| 1951 | Saint Kitts and Nevis | ||||
| 1952 | Saint Kitts and Nevis | ||||
| 1953 | Saint Kitts and Nevis | ||||
| 1954 | Saint Kitts and Nevis | ||||
| 1955 | Saint Kitts and Nevis | ||||
| 1956 | Saint Kitts and Nevis | ||||
| 1957 | Saint Kitts and Nevis | ||||
| 1958 | Saint Kitts and Nevis | ||||
| 1959 | Saint Kitts and Nevis | ||||
| 1985 | Antigua | Saint Kitts | 1 - 0 | Antigua | |
| 1986 | British Virgin Islands | Antigua | |||
| 1994 | Antigua | 1 - 0 | Saint-Martin | ||
| 1995 | Saint Kitts | Antigua | |||
| 1996 | Antigua | Saint Kitts | Antigua | ||
| 1997 | Saint Kitts | Saint Kitts | 2 - 0 | Antigua and Barbuda | |
| 1998 | Sint Maarten | Saint Kitts | 3 - 1 | Antigua | |
| 1999 | Antigua | Saint Kitts | 3 - 2 | Antigua | |
| 2000 | not held | ||||
| 2001 | Saint Thomas | Saint Kitts | 2 - 0 | Antigua | |
| 2002 | Antigua | Saint Kitts | 2 - 0 | Antigua and Barbuda | |