| 2024/25 | St. Frances Academy | Mount de Sales Academy | Glenelg Country School |
| 2023 -24 | McDonogh School | Gerstell Academy | Indian Creek |
| 2022-23 | McDonogh School | St. Mary's High School | Indian Creek |
| 2021-22 | McDonogh School | B1: Our Lady of Mt Carmel | Friends School |
| | B2: Mercy High School | |
| 2019-20 | St. Frances | St. Paul's School for Girls | Bryn Mawr School |
| 2018-19 | St. Frances | St.Paul’s School for Gis | The Catholic High School |
| 2017-18 | St. Frances | Institute of Notre Dame | Bryn Mawr School |
| 2016-17 | St. Frances | St. John's Catholic Prep | Indian Creek |
| 2015-16 | St. Frances | St. John's Catholic Prep | Garrison Forest |
| 2014-15 | McDonogh | Annapolis Area Christian | Garrison Forest |
| 2013-14 | McDonogh | Severn | St. Timothy's |
| 2012-13 | Archbishop Spalding | St. Mary's | St. Timothy's |
| 2011-12 | McDonogh | John Carroll | Annapolis Area Christian |
| 2010-11 | Archbishop Spalding | Notre Dame Prep | St. John's Catholic Prep |
| 2009-10 | St. Frances | Severn | St. John's Catholic Prep |
| 2008-09 | Seton Keough | St. Paul's School for Girls | Friends |
| 2007-08 | St. Frances | Severn | Baltimore Lutheran |
| 2006-07 | St. Frances | St. Vincent Pallotti | Annapolis Area Christian |
| 2005-06 | St. Frances | St. Vincent Pallotti | Our Lady of Mt. Carmel |
| 2004-05 | St. Frances | Severn | St. Timothy's |
| 2003-04 | St. Frances | Severn | Arlington Baptist |
| 2002-03 | St. Frances | Chapelgate Christian | Arlington Baptist |
| 2001-02 | Archbishop Spalding | Chapelgate Christian | Catholic High |
| 2000-01 | St. Frances | St. John's Catholic Prep | Beth Tfiloh |
| 1999-00 | Seton Keough | Notre Dame Prep | Towson Catholic |
