| A CONFERENCE | B CONFERENCE | C CONFERENCE | |||
| 2016 | St. Frances | St. Vincent Pallotti | St. John’s Catholic Prep | ||
| 2015 | Gilman | John Carroll | Annapolis Area Christian | ||
| 2014 | Gilman McDonogh | Archbishop Curley | St. Vincent Pallotti | ||
| 2013 | McDonogh | St. Paul’s | St. John’s Catholic Prep | ||
| 2012 | Gilman | St. Paul’s | St. Frances | ||
| 2011 | Gilman | Annapolis Area Christian | St. Frances | ||
| 2010 | Calvert Hall | Archbishop Spalding | Annapolis Area Christian | ||
| 2009 | Gilman | Archbishop Spalding | Annapolis Area Christian | ||
| 2008 | Loyola Blakefield | St. Mary’s | St. John’s Catholic Prep | ||
| 2007 | Mount St. Joseph Loyola Blakefield | St. Mary’s | Baltimore Lutheran St. John’s Catholic Prep | ||
| 2006 | Gilman Loyola Blakefield McDonogh | Archbishop Spalding | — | ||
| 2005 | Gilman | Archbishop Spalding | — | ||
| 2004 | Gilman | Archbishop Curley | St. Vincent Pallotti Boys’ Latin | ||
| 2003 | Loyola Blakefield | Archbishop Curley St. Paul’s Severn | Boys’ Latin John Carroll | ||
| 2002 | Gilman | Gold Division St. Mary’s St. Paul’s Severn Silver Division | — | ||
| 2001 | Gilman McDonogh | Gold Division Archbishop Curley Severn Silver Division | — | ||
| 2000 | Gilman | Gold Division Archbishop Curley Cardinal Gibbons Silver Division | — | ||
| 1999 | Gilman | McDonogh | — | ||
| 1998 | Gilman | McDonogh | — | ||
| 1997 | Loyola Blakefield | McDonogh | — | ||
| 1996 | St. Mary’s Loyola Blakefield Mount St. Joseph | St. Paul’s | — | ||
| 1995 | Mount St. Joseph St. Mary’s | St. Paul’s | — | ||
a
NOTES:
- From 2000 through 2002 the MIAA B Conference was divided into Gold & Silver divisions, with each division crowning its own champion.
- The MIAA did not field a C Conference from 1995 through 2002, nor 2005 and 2006.
- The MIAA began conducting a championship game in the B Conference in 2005 and has had a championship game in that conference each year since.
- The first ever championship games for the MIAA A and C Conferences were conducted in 2011.
- The MIAA held a championship game in the MIAA A Conference in 2011 and 2012, but discontinued it prior to the 2013 season, reverting back to best record to determine the league champion. At the same time, the league discontinued a rule that would break ties for the best record via head-to-head results. Starting in 2013, all teams tied for the best record are declared co-champions.
