| 2024 | Bryn Mawr | Arch. Spalding /Park School | Friends School |
| 2023 | McDonogh School | Arch. Spalding /Park School | Beth Tfiloh |
| 2022 | McDonogh School | Park School | |
| 2021 | McDonogh School | Archbishop Spalding | |
| 2019 | Garrison Forest School | Notre Dame Prep | |
| 2018 | Bryn Mawr | Archbishop Spalding | |
| 2017 | Garrison Forest School | Glenelg Country School | |
| 2016 | Bryn Mawr | Glenelg Country School | |
| 2015 | Bryn Mawr | Glenelg Country School | |
| 2014 | McDonogh | John Carroll | |
| 2013 | Bryn Mawr | Mount de Sales | |
| 2012 | Roland Park Country | Mount de Sales | |
| 2011 | Roland Park Country | Friends | |
| 2010 | Roland Park Country | Friends | |
| 2009 | Roland Park Country | McDonogh | |
| 2008 | Bryn Mawr | St. Paul's School for Girls | |
| Roland Park Country | | |
| 2007 | Bryn Mawr | Severn | |
| Notre Dame Prep | | |
| 2006 | Bryn Mawr | Severn | |
| 2005 | Bryn Mawr | Glenelg Country | |
| Roland Park Country | | |
| 2004 | St. Paul's School for Girls | Friends | |
| 2003 | Bryn Mawr | Friends | |
| 2002 | Roland Park Country | Park | |
| 2001 | McDonogh | St. Paul's School for Girls | |
| 2000 | McDonogh | St. Paul's School for Girls | |
| 1999 | McDonogh | -- | |
