| Conaree United | Season 2023/2024 | 3 Players/Coaches |
| Conaree United | Season 2022/2023 | 2 Players/Coaches |
| Conaree United | Season 2021/2022 | 1 Players/Coaches |
| Conaree United | Season 2020/2021 | 1 Players/Coaches |
| Conaree United | Season 2018/2019 | 1 Players/Coaches |
| Conaree United | Season 2017/2018 | 2 Players/Coaches |
| Conaree United | Season 2016/2017 | 2 Players/Coaches |
| Conaree United | Season 2015/2016 | 2 Players/Coaches |
| Conaree United | Season 2014/2015 | 2 Players/Coaches |
| Conaree United | Season 2013/2014 | 1 Players/Coaches |
| Conaree United | Season 2012/2013 | 2 Players/Coaches |
| Conaree United | Season 2011/2012 | 2 Players/Coaches |
| Conaree United | Season 2010/2011 | 4 Players/Coaches |
| Conaree United | Season 2009/2010 | 2 Players/Coaches |
| Conaree United | Season 2008/2009 | 1 Players/Coaches |
| Conaree United | Season 2007/2008 | 2 Players/Coaches |
| Conaree United | Season 2006/2007 | 2 Players/Coaches |
| Conaree United | Season 2005/2006 | 1 Players/Coaches |
| Conaree United | Season 2004/2005 | 1 Players/Coaches |
| Conaree United | Season 2003/2004 | 1 Players/Coaches |
| Conaree United | Season 2002/2003 | 1 Players/Coaches |
| Conaree United | Season 2001/2002 | 1 Players/Coaches |
| Conaree United | Season 2000/2001 | 1 Players/Coaches |
| Conaree United | Season 1999/2000 | 1 Players/Coaches |
| Conaree United | Season 1998/1999 | 1 Players/Coaches |
| Conaree United | Season 1997/1998 | 1 Players/Coaches |
| Conaree United | Season 1996/1997 | 1 Players/Coaches |
| Conaree United | Season 1995/1996 | 1 Players/Coaches |
| Conaree United | Season 1994/1995 | 1 Players/Coaches |
| Conaree United | Season 1993/1994 | 1 Players/Coaches |
| Conaree United | Season 1992/1993 | 1 Players/Coaches |
| Conaree United | Season 1991/1992 | 1 Players/Coaches |
| Conaree United | Season 1990/1991 | 1 Players/Coaches |
| Conaree United | Season 1989/1990 | 1 Players/Coaches |
| Conaree United | Season 1988/1989 | 1 Players/Coaches |
| Conaree United | Season 1987/1988 | 1 Players/Coaches |
St. Kitts & Nevis