| George Town SC | Season 2022/2023 | 1 Players/Coaches |
| George Town SC | Season 2018/2019 | 1 Players/Coaches |
| George Town SC | Season 2017/2018 | 1 Players/Coaches |
| George Town SC | Season 2007/2008 | 1 Players/Coaches |
| George Town SC | Season 2006/2007 | 1 Players/Coaches |
| George Town SC | Season 2005/2006 | 4 Players/Coaches |
| George Town SC | Season 2004/2005 | 4 Players/Coaches |
| George Town SC | Season 2003/2004 | 4 Players/Coaches |
| George Town SC | Season 2002/2003 | 4 Players/Coaches |
| George Town SC | Season 2001/2002 | 2 Players/Coaches |
Cayman Islands