| A CONFERENCE | | B CONFERENCE | | C CONFERENCE |
| 2016-17 | Mount St. Joseph | | St. Paul’s | | Key School |
| 2015-16 | St. Frances | | St. John’s Catholic Prep | | Saints Peter & Paul |
| 2014-15 | Calvert Hall | | Boys’ Latin | | Indian Creek |
| 2013-14 | Mount St. Joseph | | St. Paul’s | | Indian Creek |
| 2012-13 | St. Frances | | St. Vincent Pallotti | | Indian Creek |
| 2011-12 | John Carroll | | Gilman | | St. John’s Catholic Prep |
| 2010-11 | John Carroll | | Glenelg Country | | Chapelgate Christian |
| 2009-10 | St. Frances
| | St. Paul’s
| | Chapelgate Christian
|
| 2008-09 | St. Frances
| | St. Mary’s
| | Saints Peter & Paul
|
| 2007-08 | Towson Catholic
| | Mount Carmel
| | Key School |
| 2006-07 | Towson Catholic
| | St. Mary’s | | Glenelg Country |
| 2005-06 | Mount St. Joseph
| | Mount Carmel
| | Park School
|
| 2004-05 | Mount St. Joseph
| | Gilman | | Mount Carmel
|
| 2003-04 | Archbishop Spalding
| | Gilman | | Chapelgate Christian
|
| 2002-03 | Mount St. Joseph
| | St. Mary’s
| | Park School
|
| 2001-02 | Archbishop Spalding
| | St. Paul’s
| | Arlington Baptist
|
| 2000-01 | Towson Catholic
| | Archbishop Curley
| | Friends |
| 1999-00 | Arch. Spalding/Tow. Catholic
| | McDonogh | | Beth Tfiloh
|
| 1998-99 | Towson Catholic
| | McDonogh | | Chapelgate Christian |
| 1997-98 | Towson Catholic
| | McDonogh | | Friends |
| 1996-97 | Loyola Blakefield
| | St. Paul’s
|
| Archbishop Spalding
|
| 1995-96 | Calvert Hall
| | St. Paul’s | | Archbishop Curley |
