| A CONFERENCE | | B CONFERENCE | | C CONFERENCE |
| 2010 | McDonogh | | Bryn Mawr | | Chapelgate Christian |
| 2009 | Archbishop Spalding
| | Bryn Mawr
| | Annapolis Area Christian
|
| 2008 | Archbishop Spalding | | Friends | | Annapolis Area Christian
|
| 2007 | St.Vincent Pallotti | | Maryvale Prep
| | Annapolis Area Christian
|
| 2006 | Archbishop Spalding
| | Maryvale Prep
| | Annapolis Area Christian
|
| 2005 | John Carroll | | Severn
| | Chapelgate Christian |
| |
| 2004 | John Carroll | | St. John’s Prospect Hall
| | Chapelgate Christian |
| 2003 | Notre Dame Prep
| | St. John’s Prospect Hall
| | Park School |
| 2002 | St. Mary’s
| | Maryvale Prep | | — |
| |
| 2001 | St. Mary’s
| | St. John’s Prospect Hall | | — |
| 2000 | St. Mary’s | | St. John’s Prospect Hall
| | —
|
| 1999 | John Carroll | | Mount Carmel
| | — |
