Cayman Islands Digicel Cup
From Infogalactic: the planetary knowledge core
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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
Performance By Club
| Club | Winners | Runners-up | Winning Years and Runner-Up Years |
| George Town SC | 2 | 2 | 2006, 2008, 2010, 2011 |
| Elite SC | 2 | 1 | 2009, 2012, 2013 |
| Scholars International | 2 | 1 | 2007, 2009, 2013 |
| Roma United | 1 | 1 | 2008, 2011 |
| Western Union FC | 1 | - | 2006 |
| Bodden Town | - | 2 | 2010, 2012 |
| Tigers FC | - | 1 | 2007 |
