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.).

A new edition will be played in August 2014 with 8 teams.^[1]

The 2014 Leeward Islands Football Tournament, originally slated for August 9–17, has been postponed to a tentative date later this year.^[2]

Medalists

Men

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