All-Time MIAA champions
| All-Time MIAA Champions | |||
| Year | MIAA A | MIAA B | MIAA C |
| 2020 | —– | —– | —– |
| 2019 | *Mount St. Joseph | *St. Vincent Pallotti | —– |
| 2018 | %St. Frances | *St. Mary’s-AA | *Annapolis Area Christian |
| 2017 | *St. Frances | *St. Mary’s-AA | *Annapolis Area Christian |
| 2016 | St. Frances | *St. Vincent Pallotti | *St. John’s CP |
| 2015 | Gilman | *John Carroll | *Annapolis Area Christian |
| 2014 | McDonogh/ Gilman | *Archbishop Curley | *St. Vincent Pallotti |
| 2013 | McDonogh | *St. Paul’s | *St. John’s CP |
| 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 | *St. Mary’s-AA | St. John’s CP |
| 2007 | Mount St. Joseph/ Loyola | *St. Mary’s-AA | Balt. Lutheran, St.John’s CP |
| 2006 | Gilman/Loyola/ McDonogh | *Archbishop Spalding | —– |
| 2005 | Gilman | *Archbishop Spalding | —– |
| 2004 | Gilman | Archbishop Curley | Boys’ Latin, St. Vincent Pallotti |
| 2003 | Loyola | St. Paul’s, Severn, Archbishop Curley | Boys’ Latin, John Carroll |
| 2002 | Gilman | Gold: St. Mary’s-AA, St. Paul’s, Severn Silver: Boys’ Latin | —– |
| 2001 | Gilman/ McDonogh | Gold: Archbishop Curley, Severn Silver: John Carroll | —– |
| 2000 | Gilman | Gold: Archbishop Curley, Cardinal Gibbons Silver: McDonogh | —– |
| 1999 | Gilman | McDonogh | —– |
| 1998 | Gilman | McDonogh | —– |
| 1997 | Loyola | McDonogh | —– |
| 1996 | St. Mary’s-AA, Loyola, Mount St. Joseph | St. Paul’s | —– |
| 1995 | Mount St. Joseph, St. Mary’s-AA | St. Paul’s | —– |
| 1994 | Mount St. Joseph, Gilman | —– | —– |
NOTES:
*-indicates won league title through a championship game.
%-St. Frances awarded MIAA A Conference title in preseason as most league opponents dropped them from the schedule.
#-Calvert Hall and Gilman tied, but Calvert Hall was awarded the championship based on head-to-head result with Gilman.
The COVID-19 pandemic wiped out the 2020 season although a few teams did play a couple of contests. … There was no MIAA C from the league’s inception in 1995 through 2002, and again in 2005 and 2006, and again in 2019. … The B Conference was broken into two divisions from 2000-2002, each crowning their own champions. … The MIAA B started a title game in 2005 and has played one every season since. The MIAA A held championship games in 2011 and 2012, but discontinued the practice after the 2012 season. The MIAA C started championship games in 2011, and the league has held one every year until 2019.