| 2024/25 | Notre Dame Prep | Roland Park Country School | Key School |
| 2023/24 | Notre Dame Prep | Roland Park Country School | Mercy High School |
| 2022/23 | Bryn Mawr | Maryvale Prep | John Carroll School |
| 2021-22 | McDonogh | Severn School | John Carroll School |
| 2019-20 | McDonogh | Maryvale Prep | The Catholic High School |
| 2018-19 | McDonogh | St. Paul's School for Girls | St. Vincent Pallotti |
| 2017-18 | McDonogh | Roland Park Country School | The Key School |
| 2016-17 | McDonogh | Roland Park Country School | The Key School |
| 2015-16 | McDonogh | St. Mary's | St. Vincent Pallotti |
| 2014-15 | Notre Dame Prep | St. Mary's | St. Vincent Pallotti |
| 2013-14 | Notre Dame Prep | Severn | Institute of Notre Dame |
| 2012-13 | McDonogh | Severn | Seton Keough |
| 2011-12 | Notre Dame Prep | Bryn Mawr | |
| 2010-11 | Notre Dame Prep | Bryn Mawr | |
| 2009-10 | McDonogh | St. Paul's School for Girls | |
| 2008-09 | McDonogh | Severn | |
| 2007-08 | McDonogh | Archbishop Spalding | |
| 2006-07 | McDonogh | Archbishop Spalding | |
| 2005-06 | McDonogh | Institute of Notre Dame | |
| 2004-05 | McDonogh | -- | |
| 2003-04 | McDonogh | -- | |
| 2002-03 | McDonogh | -- | |
| 2001-02 | Notre Dame Prep | -- | |
| 2000-01 | Notre Dame Prep | -- | |
| 1999-00 | Notre Dame Prep | -- | |
