| Year | Dave Harmon Freedom Award | DHFA Notes | Ed Thompson Liberty Award | ETLA Notes |
| 2025 | Tim Johnson | For stepping up to help with communications, particularly his fantastic work with press releases. | H.O.T. Government | For their efforts in holding government accountable and promoting an honest, open and transparent government. |
| 2024 | Nate Gall | For tireless efforts organizing LPWI conventions. | Ann Batiza | For her efforts to free Julian Assange from unjust detention and prosecution. |
| 2023 | Scott Behrmann | For impact on Fox Valley Libertarian Party and campaign for Jacob VendenPlas. | Fox Wolf Watershed Alliance | For efforts to clean up Fox and Wolf Rivers including role of Fox Valley Libertarian Party within organization. |
| 2022 | Jim Sewell and George Meyers | For work on $1B school district referendum in Racine, suing for voting records to analyze vote counts, getting denied access to registrations; as well as their work for SE Wisconsin Libertarians | Concerned Veterans for America (Sam Rogers) | Sam Rogers is Coalitions Director for Concerned Veterans for America in Wisconsin which advocates for veterans' issues, including accountability in military affairs and a withdrawal from Afghanistan. |
| 2021 | Mike Hammond | For past years' service, Mike has gone above and beyond, getting a lot of people involved, building the party. | LEAP (Law Enforcement Action Partnership) | For work for drug policy and criminal justice reforms |
| 2020 | Nate Gall | For irreplaceable efforts running convention, the LPWI's largest event of the year, within budget. Work on Harvest Fest and MREF | Ruby's Pantry (Len Sayer) | For work distributing food to poor without government assistance and despite obstacles from City of Waupaca zoning. |
| 2019 | Brian Defferding | Elected libertarian who consistently, through his actions on the campaign trail, affiliate, and community service, has exemplified what it means to be libertarian. | Shanyell McCloud | For work with Clean Slate Milwaukee, a non-profit organization that works towards changing expungement laws in Wisconsin as well as assisting individuals in removing non-violent convictions from their records, which opens employment and education opportunities. |
| Dave Harmon Freedom Award is for service and dedication to working with the LPWI. | Ed Thompson liberty award is for a business, organization, or individual who exemplifies Libertarian principles in something they do/did. | |||