| A CONFERENCE | | B CONFERENCE | | C CONFERENCE |
| 2017 | Loyola Blakefield | | Boys’ Latin | | St. John’s Catholic Prep |
| 2016 | Archbishop Spalding | | Boys’ Latin | | St. John’s Catholic Prep |
| 2015 | Archbishop Spalding | | St. Mary’s | | St. John’s Catholic Prep |
| 2014 | Archbishop Spalding | | St. Mary’s | | St. John’s Catholic Prep |
| 2013 | Calvert Hall | | Glenelg Country | | Chapelgate Christian |
| 2012 | Calvert Hall | | Annapolis Area Christian | | St. John’s Catholic Prep |
| 2011 | Archbishop Spalding | | Mount Carmel | | St. John’s Catholic Prep |
| 2010 | Gilman | | Park School | | Key School |
| 2009 | Calvert Hall | | Baltimore Lutheran | | St. Frances |
| 2008 | Calvert Hall | | Boys’ Latin | | Beth Tfiloh School |
| 2007 | Calvert Hall | | St. Mary’s | | Glenelg Country |
| 2006 | Calvert Hall | | St. Vincent Pallotti | | Annapolis Area Christian |
| 2005 | Calvert Hall | | St. Vincent Pallotti | | — |
| 2004 | Mount St. Joseph | | St. Mary’s | | — |
| 2003 | St. Paul’s | | Chapelgate Christian | | — |
| 2002 | St. Paul’s | | Severn School | | — |
| 2001 | Archbishop Curley | | Mount Carmel | | — |
| 2000 | Calvert Hall | | Cardinal Gibbons | | — |
| 1999 | Archbishop Curley | | Cardinal Gibbons | | — |
| 1998 | Calvert Hall | | Chapelgate Christian | | — |
| 1997 | Calvert Hall | | Park School | | — |
| 1996 | Gilman | | St. Paul’s | | — |
