Varsity Cross Country Champions
| "A" Conference | "B" Conference | "C" Conference | |||
| 2023 | McDonogh School | Mercy High School | Gerstell Academy | ||
| 2022 | McDonogh School | Mercy High School | The Catholic High School | ||
| 2021 | McDonogh School | Severn School | Mercy High School | ||
| 2019 | Maryvale Prep | The John Carroll School | St. Vincent Pallotti | ||
| 2018 | Mount de Sales Academy | St. Mary's HS | Park School | ||
| 2017 | Archbishop Spalding | Roland Park Country | Glenelg Country | ||
| 2016 | Maryvale Prep | Roland Park Country | Park School | ||
| 2015 | Maryvale Prep | St. Paul's School for Girls | Oldfields School | ||
| 2014 | McDonogh | Severn | Oldfields School | ||
| 2013 | John Carroll | Maryvale Prep | Garrison Forest | ||
| 2012 | Archbishop Spalding | Bryn Mawr | Garrison Forest | ||
| 2011 | Archbishop Spalding | Mount de Sales | Annapolis Area Christian | ||
| 2010 | McDonogh | Mount de Sales | Glenelg Country | ||
| 2009 | John Carroll | St. Mary's | -- | ||
| 2008 | Notre Dame Prep | Severn | -- | ||
| 2007 | Notre Dame Prep | Institute of Notre Dame | -- | ||
| 2006 | John Carroll | Institute of Notre Dame | -- | ||
| 2005 | Notre Dame Prep | Seton Keough | -- | ||
| 2004 | Mercy | Glenelg Country | -- | ||
| 2003 | Bryn Mawr | St. Paul's School for Girls | -- | ||
| 2002 | Bryn Mawr | St. John's Catholic Prep | -- | ||
| 2001 | Bryn Mawr | Glenelg Country | -- |