| A CONFERENCE | | B CONFERENCE | | C CONFERENCE |
| 2017 | Calvert Hall | | John Carroll | | Beth Tfiloh |
| 2016 | McDonogh | | John Carroll | | St. Vincent Pallotti |
| 2015 | St. Mary’s | | John Carroll | | Indian Creek |
| 2014 | Boys’ Latin | | Saints Peter & Paul | | Indian Creek |
| 2013 | Loyola Blakefield | | Saints Peter & Paul | | Gerstell Academy |
| 2012 | Calvert Hall | | Saints Peter & Paul | | Gerstell Academy |
| 2011 | Gilman | | Friends | | Baltimore Lutheran |
| 2010 | St. Paul’s
| | John Carroll
| | Baltimore Lutheran
|
| 2009 | Gilman | | Annapolis Area Christian
| | Baltimore Lutheran
|
| 2008 | Loyola Blakefield
| | Archbishop Curley
| | Cardinal Gibbons
|
| 2007 | Loyola Blakefield
| | Archbishop Curley
| | Chapelgate Christian
|
| 2006 | Boys’ Latin
| | St. Vincent Pallotti | | Chapelgate Christian
|
| 2005 | McDonogh | | Park School
| | Glenelg Country |
| 2004 | St. Paul’s
| | John Carroll
| | Glenelg Country
|
| 2003 | Calvert Hall
| | John Carroll
| | Chapelgate Christian
|
| 2002 | Boys’ Latin
| | Archbishop Spalding
| | Chapelgate Christian
|
| 2001 | Loyola Blakefield
| | Archbishop Spalding
| | Saints Peter & Paul
|
| 2000 | Gilman | | Archbishop Spalding | | Saints Peter & Paul
|
| 1999 | McDonogh | | Friends | | Annapolis Area Christian |
| 1998 | Gilman | | Friends | | Annapolis Area Christian |
| 1997 | Boys’ Latin
| | Friends | | — |
| 1996 | St. Mary’s
| | John Carroll
| <
/td> | — |
