| Name | Wins | Years |
| Joyce Flynn | 8 | 2005, 2007, 2011, 2012, 2014, 2015, 2018, 2020 |
| Marty Flynn, Jr. | 7 | 1995 (t), 1997, 2001, 2009, 2010, 2017, 2022 |
| Marty Flynn, Sr. | 4 | 1991, 2002, 2003, 2004 |
| Matt Flynn | 4 | 1993, 2000, 2006, 2008 |
| Joanne Flynn | 3 | 2016, 2019, 2021 |
| Mike Flynn | 2 | 1989 (t), 1996 |
| Chris Flynn | 2 | 1998, 2013 |
| Sally Doederlein | 1 | 1989 (t) |
| Ted Doederlein | 1 | 1992 |
| Pete Flynn | 1 | 1994 |
| Mary Flynn | 1 | 1990 |
| Rosanne Flynn | 1 | 1995 |