Legionnaire of the Year
| 2025 | Harvey Phillips |
| 2024 | Morris Sadicario |
| 2023 | Morris Sadicario |
| 2022 | Keith Lovell |
| 2021 | Jerry Schultz |
| 2020 | Jerry Schultz |
| 2019 | Jerry Schultz |
| 2018 | Gene Sheets |
| 2017 | Christine Robbins |
| 2016 | Bill Robbins and Phil Ingwell |
| 2015 | Don Brinkmeier |
| 2014 | Thomas Stolarczyk |
| 2013 | Don Brinkmeier |
| 2012 | Thomas Stolarczyk |
| 2011 | Phil Ingwell |
| 2010 | Ed Burke |
| 2009 | Bud Mautz |
Volunteer of the Year
| 2024 | Leo Gabriel |
| 2023 | Colleen Cotter |
| 2022 | Jessica Ecker and Allison Maly |
| 2021 | Bill Brendler |
| 2020 | Tim Dollak [Woodman's] |
| 2019 | Barb Johnson |
| 2018 | Mary Hanson Frame |
| 2017 | Victoria Boerke & Family |
| 2016 | Mary Hanson Frame |
| 2015 | Colleen Cotter & Matthew Ley (Scout Trp 149) |
| 2014 | Dave Ruland |
| 1995 | Don "Pierre" McNicol, Jerry "JP" Paulus & Loren Olson |
| 1994 | Roger D. Horge, Arlene Krinkey, Herman Nellen, Kristi B. & Loren Olson |
| 1993 | Loren Olson |
| 1992 | Loren Olson |
Law Enforcement Officer of the Year
|
2024 |
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| 2023 | |
| 2022 | |
| 2021 | Mackenzie Miller, Sun Prairie Police |
| 2020 | |
| 2019 | |
| 2018 | Dane County Deputy Sheriff Jeffrey Thiel |
| 2017 | Dane County Deputy Sheriff Josalyn Langley |
| 2016 | Cheryl Patty, Dane County Sheriff's Office |