| Year | Cupid | Co-Cupid |
| 1982 | Wayne Norman | |
| 1983 | Claire Meikle | |
| 1984 | Dick Nassiff, Sr. | |
| 1985 | Mary Josephs | |
| 1986 | Harold Hanka | |
| 1987 | Ron Pires | |
| 1988 | Laura Knott-Twine | |
| 1989 | David Carter | |
| 1990 | Bill Pike | |
| 1991 | Kathy Clark | |
| 1992 | Cora Moore | |
| 1993 | Merle Risley | Lynn Duvall |
| 1994 | Don Berkowitz | |
| 1995 | Shawn Maynard | |
| 1996 | Bob Mustard | |
| 1997 | Bill Anthony | Ruth Ridgeway |
| 1998 | Erni Kuter | |
| 1999 | Bev York | |
| 2000 | Linda Riquier | |
| 2001 | Ray Aramini | |
| 2002 | Paul Kaplitz | |
| 2003 | Jean de Smet | |
| 2004 | Virginia Darrow | Jason Altieri |
| 2005 | Rosa Tirado | |
| 2006 | Robert Horrocks | Pam Horrocks |
| 2007 | Ernie Eldridge | |
| 2008 | Lynn White | |
| 2009 | Mary Lou Devivo | |
| 2010 | Linda Sypher | |
| 2011 | Steve Kenton | Faith Kenton |
| 2012 | Bruce John | |
| 2013 | Karen Gilbransen | |
| 2014 | Munere "Mooney" Haddad | |
| 2015 | John Lescoe | Brian Crudden |
| 2016 | David Wollner | |
| 2017 | Yolanda Negron | Sandy Reed |
| 2018 | James Baran | |
| 2019 | Joseph Rasicott | |
| 2020 | Alicia Rivera | |
| 2021 | Windham Area Healthcare Workers and First Responders | |
| 2022 | ~~~~~~~~~ |
