| Year | Winner |
| 2021 | Joanne Flynn |
| 2020 | Joyce Flynn |
| 2019 | Joanne Flynn |
| 2018 | Joyce Flynn |
| 2017 | Marty Flynn, Jr. |
| 2016 | Joanne Flynn |
| 2015 | Joyce Flynn |
| 2014 | Joyce Flynn |
| 2013 | Chris Flynn |
| 2012 | Joyce Flynn |
| 2011 | Joyce Flynn |
| 2010 | Marty Flynn, Jr. |
| 2009 | Marty Flynn, Jr. |
| 2008 | Matt Flynn |
| 2007 | Joyce Flynn |
| 2006 | Matt Flynn |
| 2005 | Joyce Flynn |
| 2004 | Marty Flynn, Sr. |
| 2003 | Marty Flynn, Sr. |
| 2002 | Marty Flynn, Sr. |
| 2001 | Marty Flynn, Jr. |
| 2000 | Matt Flynn |
| 1999 | In Memory of Pete Flynn |
| 1998 | Chris Flynn |
| 1997 | Marty Flynn, Jr |
| 1996 | Mike Flynn |
| 1995 | Rosanne Flynn/Marty Flynn, Jr |
| 1994 | Pete Flynn |
| 1993 | Matt Flynn |
| 1992 | Ted Doederlein |
| 1991 | Marty Flynn, Sr. |
| 1990 | Mary Flynn |
| 1989 | Sally Doederlein/Mike Flynn |