Legionnaire of the Year
| 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 |
Volunteer of the Year
| 2024 | Colleen Cotter |
| 2023 | Colleen Cotter |
| 2022 | Jessica Ecker and Allison Maly |
| 2021 | Bill Brendler |
| 2020 | Tim Dollak [Woodman's] |
| 2019 | Barb Johinous |
| 2018 | Mary Hanson Frame |
| 2018 | |
| 2017 | Victoria Boerke and Family |
| 2016 | Mary Hanson Frame |
| 2015 | Colleen Cotter and Matthew Ley |
| 2014 | Dave Ruland |
Law Enforcement Officer of the Year
|
2024 |
|
| 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 |