|All-Time MIAA Champions|
|Year||MIAA A||MIAA B||MIAA C|
|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||—–|
|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||—–|
|1996||St. Mary’s-AA/ Loyola/ Mount St. Joseph||St. Paul’s||—–|
|1995||Mount St. Joseph/ St. Mary’s-AA||St. Paul’s||—–|
*-indicates won league title through a championship game.
#-Calvert Hall and Gilman tied, but Calvert Hall was awarded the championship based on head-to-head result with Gilman.
There was no MIAA C from the league’s inception in 1995 through 2002, and again in 2005 and 2006. … 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 since.