Boston Annual Top Hat Award Winners
| 2019 | Donald Marinelli | St. Michaels Conference, North Andover |
| 2018 | Robert Curran | St. Joseph Conference, Wakefield |
| 2017 | William Kelly | Holy Name Conference, West Roxbury |
| 2016 | Patricia Daily | St. Michaels Conference, Lowell |
| 2015 | Frank Walsh | St. John Conference, Canton |
| 2014 | Richard T. LaPorte | St. Michaels Conference, Lowell |
| 2013 | William Pye | Sacred Heart, Middleboro |
| 2012 | Marjorie Maguire | St. Mary’s Conference, Waltham |
| 2011 | James McGilivray | St. Patrick’s Conference, Natick |
| 2010 | Edward J. Downs | St. Agnes, Arlington |
| 2009 | Chanel Vachon | St. Mary of the Assumption, Lawrence |
| 2008 | Brendan Fleming | Holy Family Conference, Lowell |
| 2007 | Lloyd Wajda | St. Monica’s Conference, Methuen |
| 2006 | Cynthia Hollenbeck | St. Augustine’s Conference, Andover |
| 2005 | William Philpot | St. Ann’s Conference, Somerville |
| 2004 | Robert Dolan | St. Bridget’s Conference, Arlington |
| 2002 | John J. O’Malley | Sacred Heart’s Conference, Lynn |