| Tobago United | Season 2011/2012 | 1 Players/Coaches |
| Tobago United | Season 2010/2011 | 1 Players/Coaches |
| Tobago United | Season 2009/2010 | 4 Players/Coaches |
| Tobago United | Season 2008/2009 | 7 Players/Coaches |
| Tobago United | Season 2007/2008 | 7 Players/Coaches |
| Tobago United | Season 2006/2007 | 6 Players/Coaches |
| Tobago United | Season 2005/2006 | 3 Players/Coaches |
| Tobago United | Season 2004/2005 | 4 Players/Coaches |
| Tobago United | Season 2003/2004 | 1 Players/Coaches |
| Tobago United | Season 2002/2003 | 1 Players/Coaches |
Trinidad & Tobago