Cayman Islands Digicel Cup

The Cayman Islands Digicel Cup is a cup of the Cayman Islands football, first held in 2006. It is sponsored by Digicel.

Winners

 * 2005/06 : Money Express 2-0 George Town SC
 * 2006/07 : Scholars International bt Tigers FC
 * 2007/08 : Roma United 1-0 George Town SC
 * 2008/09 : Elite SC 4-1 Scholars International
 * 2009/10 : George Town SC 2-1 Bodden Town
 * 2010/11 : George Town SC 3-1 Roma United
 * 2011/12 : Elite SC 2-0 Bodden Town
 * 2012/13 : Scholars International 0-0 (aet, 7-6 pen) Elite SC


 * President's Cup
 * 2013/14 : Bodden Town FC 2-1 George Town SC
 * 2014/15 : Bodden Town FC 1-1 Roma United SC [aet, 3-1 pen]
 * 2015/16 : Roma United SC 2-1 Bodden Town FC [aet]
 * 2016/17 : Scholars International 4-1 Bodden Town FC