TEAM CHAMPIONS
| A CONFERENCE | B CONFERENCE | C CONFERENCE | ||
| 2016 | Mount St. Joseph | Park School | Friends School | |
| 2015 | Mount St. Joseph | Boys’ Latin | Friends School | |
| 2014 | Loyola Blakefield | Boys’ Latin | ||
| 2013 | Loyola Blakefield | Glenelg Country | ||
| 2012 | Loyola Blakefield | Baltimore Lutheran | ||
| 2011 | Loyola Blakefield | St. Paul’s | ||
| 2010 | Loyola Blakefield | St. Mary’s | ||
| 2009 | Loyola Blakefield | St. Paul’s | ||
| 2008 | Calvert Hall | Annapolis Area Christian | ||
| 2007 | Calvert Hall | Annapolis Area Christian | ||
| 2006 | Loyola Blakefield | St. Paul’s | ||
| 2005 | Loyola Blakefield | Severn | ||
| 2004 | Archbishop Spalding | St. Mary’s | ||
| 2003 | Loyola Blakefield | St. Paul’s | ||
| 2002 | Archbishop Curley | Glenelg Country | ||
| 2001 | McDonogh | St. Mary’s | ||
| 2000 | Loyola Blakefield | Archbishop Spalding | ||
| 1999 | Calvert Hall | Archbishop Spalding | ||
| 1998 | Loyola Blakefield | — | ||
| 1997 | Gilman/Calvert Hall/Loyola | — | ||
| 1996 | Gilman | — | ||
| 1995 | Calvert Hall | — |
I
INDIVIDUAL CHAMPIONS
| CHAMPIONS | SCHOOL | ||
| 2016 | Dalton Hengst | McDonogh | |
| 2015 | Dalton Hengst | McDonogh | |
| 2014 | Michael Wegner | Loyola Blakefield | |
| 2013 | Tyler Spear | Loyola Blakefield | |
| 2012 | Tyler Spear | Loyola Blakefield | |
| 2 011 | Kevin Corbusier | Loyola Blakefield | |
| 2010 | Matt Jablonski | Loyola Blaefield | |
| 2009 | Matt Jablonski | Loyola Blakefield | |
| 2008 | Zac Sullivan | Archbishop Spalding | |
| 2007 | Zac Sullivan | Archbishop Spalding | |
| 2006 | Rob Wetzel | Archbishop Spalding | |
| 2005 | Sam Jackson | Gilman | |
| 2004 | Tristram Thomas | McDonogh | |
| 2003 | Tristram Thomas | McDonogh | |
| 2002 | Tristram Thomas | McDonogh | |
| 2001 | Chris Wright | Mount St. Joseph | |
| 2000 | Dusty Lieb | Archbishop Spalding | |
| 1999 | Chris Wright | Mount St. Joseph | |
| 1998 | Chris Knott | Loyola Blakefield | |
| 1997 | Seamus Whelton | Gilman | |
| 1996 | David Chalmers | Gilman | |
| 1995 | Cory Smith | Calvert Hall |
I
MOST INDIVIDUAL CHAMPIONS BY SCHOOL
| SCHOOL | NO. OF CHAMPIONS | |
| Archbishop Spalding | 4 | |
| Loyola Blakefield | 4 | |
| McDonogh | 3 | |
| Gilman | 3 | |
| Mount St. Joseph | 2 | |
| Calvert Hall | 1 |
