Rock Diamond Award
(1995 - Present)
| Year | Winner | Former Team(s) |
| 2025 | Paul Hauser Jr. | Rubicon |
| 2024 | Wes Braunschweig | Neosho, Ashippun, Clyman |
| 2023 | Ross Roeseler | Hustisford |
| 2022 | Tim Fitzsimmons | Clyman |
| 2021 | Dave Zimmerman | Slinger, Pardeeville |
| 2020 | None Selected - COVID | |
| 2019 | Gary Schwefel | Lebanon |
| 2018 | Steve Salter | Slinger |
| 2017 | Lynn Held | Lebanon, Hustisford |
| 2016 | Phil Nehls | Hustisford, Clyman, Rubicon |
| 2015 | Steve Lehman | Juneau, Clyman |
| 2014 | Neal Kohlhoff | Clyman |
| 2013 | Ken Held | Neosho, Slinger |
| 2012 | Bill Bergin | Lebanon |
| 2011 | Don Christopherson | Ashippun |
| 2010 | None Selected | |
| 2009 | Hugh Roberts | Randolph |
| 2008 | Jim Pirkel | Watertown |
| 2007 | Jim Braunschweig | Johnson Creek |
| 2006 | Don Held | Rubicon, Hustisford, Lebanon |
| 2005 | Gib Youngbeck | Mayville |
| 2004 | Rich Block | Watertown |
| 2003 | Bob Kuehl | Hustisford |
| 2002 | Will Eske | Lebanon |
| 2001 | Howard "Sam" Narges | Long Lake |
| 2000 | Fran Hofmaier | Slinger |
| 1999 | Carl Heimerl | Rubicon |
| 1998 | Bud Bellon | Former Commissioner, RR Old-Timers Secretary |
| 1997 | L.O. "Ozzie" Bloohm | Brownsville |
| 1996 | Elmer Marks | Former Commissioner, Hustisford, Ashippun |
| 1995 | Norm "Lefty" Bischoff | Juneau |
