| A CONFERENCE | B CONFERENCE | C CONFERENCE | |||
| 2016 | Calvert Hall | Severn School | Concordia Prep | ||
| 2015 | McDonogh | Severn School | Indian Creek | ||
| 2014 | Loyola Blakefield | Severn School | Indian Creek | ||
| 2013 | McDonogh | Gerstell Academy | Key School | ||
| 2012 | Loyola Blakefield | Boys’ Latin | Gerstell Academy | ||
| 2011 | McDonogh | St. Paul’s | Gerstell Academy | ||
| 2010 | Gilman | St. Paul’s | Baltimore Lutheran | ||
| 2009 | Mount St. Joseph | Annapolis Area Christian | Chapelgate Christian | ||
| 2008 | McDonogh | Boys’ Latin | Baltimore Lutheran | ||
| 2007 | McDonogh | Boy’s Latin | Baltimore Lutheran | ||
| 2006 | Archbishop Curley | Severn School | Chapelgate Christian | ||
| 2005 | Loyola Blakefield Mount St. Joseph | St. Mary’s | Chapelgate Christian | ||
| 2004 | McDonogh | Boys’ Latin | Glenelg Country | ||
| 2003 | Calvert Hall | Boys’ Latin | Saints Peter & Paul | ||
| 2002 | Calvert Hall | Boys’ Latin Severn School | Chapelgate Christian Saints Peter & Paul | ||
| 2001 | Mount St. Joseph | Gilman | Baltimore Lutheran | ||
| 2000 | McDonogh | St. Paul’s | Mount Carmel | ||
| 1999 | Archbishop Curley | Friends School | Mount Carmel | ||
| 1998 | McDonogh | Friends School | Chapelgate Christian | ||
| 1997 | Calvert Hall | St. Paul’s | Chapelgate Christian | ||
| 1996 | Calvert Hall | Boys’ Latin | Arlington Baptist Glenelg Country | ||
| 1995 | Archbishop Curley Gilman | St. Mary’s St. Paul’s | Towson Catholic | ||
