| A CONFERENCE | B CONFERENCE | ||
| 2016 | Gilman | — | |
| 2015 | Loyola Blakefield | — | |
| 2014 | Gilman | — | |
| 2013 | Gilman | — | |
| 2012 | Loyola Blakefield | — | |
| 2011 | Loyola Blakefield | St. Paul’s | |
| 2010 | Loyola Blakefield | Boys’ Latin | |
| 2009 | Calvert Hall | St. Paul’s | |
| 2008 | Gilman | Boys’ Latin | |
| 2007 | Loyola Blakefield | Archbishop Spalding | |
| 2006 | Mount St. Joseph | Boys’ Latin | |
| 2005 | Loyola Blakefield | Archbishop Spalding | |
| 2004 | Loyola Blakefield | Boys’ Latin | |
| 2003 | John Carroll | — | |
| 2002 | Calvert Hall | — | |
| 2001 | Calvert Hall | — | |
| 2000 | Calvert Hall | — | |
| 1999 | Calvert Hall | — |
