| Cudlip Winner | Year |
|---|---|
| David Gabriel | 1991 |
| Jay Utz | 1992 |
| Greg Montero | 1993 |
| Pat OConnor | 1994 |
| Dave Simprini | 1995 |
| Doug Thiede | 1996 |
| Michael Zehr | 1997 |
| Andy Mullins | 1998 |
| Rob Pennington | 1999 |
| Andrew Harrison | 2000 |
| David Melon | 2001 |
| Tom Sanders | 2002 |
| Morgan Helm | 2003 |
| Mike Burlin | 2004 |
| John Gurski | 2005 |
| Benjamin Matherne | 2006 |
| Bo Palmore | 2007 |
| Alfred Lucia | 2008 |
| David Forscey | 2009 |
| Robert Goodyear | 2010 |
| Jefferson Taylor Leonard | 2011 |
| Henry Kittredge | 2012 |
| Richard Wesnofske Jr. | 2013 |
| Henry Peltz | 2014 |
| Carl Liles | 2015 |
| Dillon Wild | 2016 |
| Justin Cooksey | 2017 |
| Zach Beim | 2018 |
| Kyle Brumbaugh | 2019 |
| Kevin Cox | 2020 |
Last Updated: February 2021