Ganador de la Copa
| Temporada | Equipo | Título | |
|---|---|---|---|
| 2021 |  | Bodden Town FC | 5. |
| 2019 |  | Elite SC | 3. |
| 2018 |  | Academy FC | 1. |
| 2017 | | Bodden Town FC | 4. |
| 2016 | | Elite SC | 2. |
| 2015 |  | Cayman Athletic SC | 1. |
| 2014 | | Elite SC | 1. |
| 2013 | | Bodden Town FC | 3. |
| 2012 |  | Scholars International | 4. |
| 2011 |  | George Town SC | 4. |
| 2010 | | George Town SC | 3. |
| 2009 | | Bodden Town FC | 2. |
| 2008 | | Scholars International | 3. |
| 2007 |  | Latinos | 2. |
| 2006 | | Scholars International | 2. |
| 2005 |  | Western Union | 1. |
| 2004 | | Latinos | 1. |
| 2003 | | Scholars International | 1. |
| 2002 | | George Town SC | 2. |
| 2001 | | Bodden Town FC | 1. |
| 1998 | | George Town SC | 1. |
| 1996 |  | East End | 1. |