| 2024 | Bryn Mawr | St. Mary's High School | Park School |
| 2023 | Garrison Forest | St. Mary's High School | Park School |
| 2022 | Garrison Forest | The John Carroll School | The Catholic High School |
| 2021 | Archbishop Spalding | St. Paul's School for Girls | St. Timothy's School |
| 2019 | Garrison Forest | The John Carroll School | Friends School |
| 2018 | Notre Dame Prep | St. Mary's High School | Key School |
| 2017 | Notre Dame Prep | St. Paul's School for Girls | Park School |
| 2016 | McDonogh | John Carroll School | Park School |
| 2015 | Archbishop Spalding | John Carroll School | Key School |
| 2014 | McDonogh | John Carroll School | St. Timothy's |
| 2013 | Archbishop Spalding | Mount de Sales | Catholic High |
| 2012 | Garrison Forest | Seton Keough | St. Timothy's |
| 2011 | Garrison Forest | Mount de Sales | St. Timothy's |
| 2010 | Garrison Forest | Glenelg Country | Annapolis Area Christian |
| 2009 | Bryn Mawr | McDonogh | Mercy |
| 2008 | Garrison Forest | McDonogh | Mercy |
| 2007 | Garrison Forest | McDonogh | Institute of Notre Dame |
| 2006 | Bryn Mawr | Maryvale Prep | Mercy |
| 2005 | Roland Park Country | Maryvale Prep | Mercy |
| | John Carroll | Baltimore Lutheran |
| 2004 | Roland Park Country | Friends | St. Timothy's |
| 2003 | St. Paul's School for Girls | Glenelg Country | -- |
| 2002 | Roland Park Country | | |
| St. Paul's School for Girls | | |
| 2001 | Bryn Mawr | | |
| St. Paul's School for Girls | | |
| 2000 | Bryn Mawr | Glenelg Country | -- |
| 1999 | Bryn Mawr | -- | -- |
