| 2024 | Maryvale Prep | Garrison Forest | Gerstell Academy |
| 2023 | Maryvale Prep | Garrison Forest | Chapelgate Chrsitian |
| 2022 | Maryvale Prep | Mercy High School | Glenelg Country School |
| 2021 | Maryvale Prep | St. John's Catholic Prep | Friends School |
| 2019 | Mount de Sales | St. Mary's | Friends School |
| 2018 | Mount de Sales | Catholic High | Indian Creek |
| 2017 | Mount de Sales | Annapolis Area Christian | St. Frances Academy |
| 2016 | Notre Dame Prep | Maryvale Prep | St. Frances Academy |
| 2015 | Mount de Sales | Roland Park Country | Annapolis Area Christian |
| 2014 | Notre Dame Prep | Roland Park Country | St. Timothy's |
| 2013 | St. Paul's School for Girls | Roland Park Country | St. John's Catholic Prep |
| 2012 | Seton Keough | Mercy | St. John's Catholic Prep |
| 2011 | Archbishop Spalding | John Carroll | Catholic High |
| 2010 | Mount de Sales | John Carroll | Friends |
| 2009 | Mount de Sales | John Carroll | St. Timothy's |
| 2008 | Mount de Sales | Notre Dame Prep | Beth Tfiloh |
| 2007 | St. Paul's School for Girls | Mercy | Annapolis Area Christian |
| 2006 | Archbishop Spalding | Bryn Mawr | Annapolis Area Christian |
| 2005 | St. Paul's School for Girls | Notre Dame Prep | Oldfields |
| 2004 | Institute of Notre Dame | Notre Dame Prep | Towson Catholic |
| 2003 | John Carroll | St. Paul's School for Girls | Roland Park Country |
| 2002 | McDonogh | John Carroll | St. Paul's School for Girls |
| 2001 | McDonogh | Mount de Sales | -- |
| 2000 | McDonogh | Our Lady of Mt. Carmel | -- |
| 1999 | Friends | St. John's Catholic Prep | -- |
