| 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 | | — | |
