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The Cayman Islands FA Cup is the top knockout tournament of the Cayman Islands football.
Winners
- 1995/96 : East End United
- 1996/97 not known
- 1997/98 : George Town SC
- 1998/99 not known
- 1999/00 not known
- 2000/01 : Bodden Town FC
- 2001/02 : George Town SC 4-0 Scholars International
- 2002/03 : Scholars International 2-1 Bodden Town FC
- 2003/04 : Latinos FC 2-1 George Town SC
- 2004/05 : Western Union FC 2-0 Scholars International
- 2005/06 : Scholars International 2-0 Money Express
- 2006/07 : Latinos FC 3-0 Elite SC
- 2007/08 : Scholars International 1-0 Elite SC
- 2008/09 : Bodden Town FC 3-1 Elite SC
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