| A CONFERENCE | B CONFERENCE | C CONFERENCE | |||
| 2017 | St. Paul’s | Boys’ Latin | Friends School | ||
| 2016 | St. Paul’s | Boys’ Latin | Friends School | ||
| 2015 | Archbishop Spalding | Severn | Annapolis Area Christian | ||
| 2014 | Archbishop Spalding | Severn | Annapolis Area Christian | ||
| 2013 | Calvert Hall | Severn | Chapelgate Christian | ||
| 2012 | Mount St. Joseph | St. Mary’s | Chapelgate Christian | ||
| 2011 | McDonogh | St. Mary’s Saints Peter & Paul | Glenelg Country | ||
| 2010 | McDonogh | Saints Peter & Paul | Glenelg Country | ||
| 2009 | McDonogh | Chapelgate Christian | — | ||
| 2008 | Gilman | St. Vincent Pallotti | — | ||
| 2007 | St. Paul’s | St. Vincent Pallotti | — | ||
| 2006 | Gilman | Annapolis Area Christian | — | ||
| 2005 | St. Paul’s | Severn | — | ||
| 2004 | Mount St. Joseph | Severn | — | ||
| 2003 | St. Paul’s | Severn | — | ||
| 2002 | St. Paul’s | Boys’ Latin | Annapolis Area Christian | ||
| 2001 | St. Paul’s | Severn | Park School | ||
| 2000 | John Carroll | Archbishop Spalding | — | ||
| 1999 | St. Paul’s | McDonogh | — | ||
| 1998 | Gilman | St. Mary’s | — | ||
| 1997 | Calvert Hall | St. Paul’s | — | ||
| 1996 | Calvert Hall | St. Paul’s | — |
I
INDIVIDUAL STROKE PLAY CHAMPIONS
| CHAMPIONS | SCHOOL | ||
| 2017 | Jack Halleron | Boys’ Latin | |
| 2016 | Eric Hall | Severn School | |
| 2015 | Chris Navarro | Archbishop Spalding | |
| 2014 | Chris Navarro | Archbishop Spalding | |
| 2013 | David Long | Mount St. Joseph | |
| 2012 | Chris Navarro | Archbishop Spalding | |
| 2011 | Sam Stewart | Gilman | |
| 2010 | Kaitlyn Rohrback | Archbishop Spalding | |
| 2009 | Jason Burton | Calvert Hall | |
| 2008 | Ben Holman | Gilman | |
| 2007 | Mike Kelen | St. Paul’s | |
| 2006 | Chris Rockwell | Gilman | |
| 2005 | Michael O’Neil | St. Paul’s | |
| 2004 | Greg Rodgers | St. Paul’s | |
| 2003 | Greg Rodgers | St. Paul’s | |
| 2002 | Alex Bruggerman | John Carroll | |
| 2001 | Greg Rodgers | St. Paul’s | |
| 2000 | Chuck Bruggerman | John Carroll | |
| 1999 | Mike Grimm | St. Paul’s | |
| 1998 | Bart DeLuca | Gilman | |
| 1997 | Jason Snyder | Calvert Hall | |
| 1996 | P.J. Singh | Gilman |
I
MOST INDIVIDUAL STROKE PLAY CHAMPIONS BY SCHOOL
| SCHOOL | NO. OF CHAMPIONS | |
| St. Paul’s | 6 | |
| Gilman | 4 | |
| John Carroll | 2 | |
| Calvert Hall | 2 | |
| Archbishop Spalding | 1 |
