| A CONFERENCE | | B CONFERENCE | C CONFERENCE |
2017 | Gilman | | Severn | Indian Creek |
2016 | Gilman | | Severn | Annapolis Area Christian |
2015 | Gilman | | Archbishop Spalding | Archbishop Curley |
2014 | Gilman | | Beth Tfiloh | Key School |
2013 | Mount St. Joseph | | Archbishop Splading | |
2012 | Mount St. Joseph | | Annapolis Area Christian | |
2011 | McDonogh | | Annapolis Area Christian | |
2010 | Gilman | | Archbishop Spalding
| |
2009 | McDonogh | | Archbishop Spalding
| |
2008 | McDonogh | | Glenelg Country
| |
2007 | Gilman | | Severn School
| |
2006 | Gilman | | Severn School
| |
2005 | McDonogh | | Beth Tfiloh
| |
2004 | McDonogh | | Archbishop Spalding
| |
2003 | Gilman | | Severn School
| |
2002 | McDonogh | | Severn School | |
2001 | Calvert Hall
| | Beth Tfiloh
| |
2000 | Gilman | | Archbishop Curley
| |
1999 | McDonogh | | Archbishop Curley
| |
1998 | Gilman | | Archbishop Curley
| |
1997 | McDonogh | | Archbishop Curley
| |
1996 | McDonogh | | — | |