| Year | Name | City, State | Time |
| 2026 | Greyson Stout | Sheboygan, WI | 51:50 |
| 2025 | Ian Nadolski | Waukesha, WI | 54:18 |
| 2024 | Grayson Stout | Sheboygan, WI | 50:33 |
| 2023 | Grayson Stout | Sheboygan, WI | 52:36 |
| 2022 | John Dewitt | Milwaukee, WI | 54:14 |
| 2019 | David Luy | Brookfield, WI | 51:48 |
| 2018 | David Luy | Brookfield, WI | 51:43 |
| 2017 | John Dewitt | Milwaukee, WI | 50:09 |
| 2016 | Tyler Sigl | Seymour, WI | 52:31 |
| 2015 | John Dewitt | Milwaukee, WI | 51:40 |
| 2014 | Tyler Sigl | Seymour, WI | 53:31 |
| 2013 | Tyler Sigl | Seymour, WI | 53:56 |
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| Year | Name | City, State | Time |
| 2026 | Leah Patterson | Oshkosh, WI | 1:01:53 |
| 2025 | Allyson Verbauwhede | Whitelaw, WI | 1:04:30 |
| 2024 | Raissa Ashman | Seymour, WI | 1:12:11 |
| 2023 | Kathy Vandehy | Menasha, WI | 57:13 |
| 2022 | Katie Gellings | North Fond du Lac, WI | 1:06:01 |
| 2019 | Laura Schmitz | Oshkosh, WI | 1:01:26 |
| 2018 | Caitlin Kowalke | Cross Plains, WI | 1:00:35 |
| 2017 | Caitlin Comfort | Verona, WI | 1:01:00 |
| 2016 | Laura Schmitz | Oshkosh, WI | 1:05:24 |
| 2015 | Caitlin Comfort | Verona, WI | 59:07 |
| 2014 | Jenny Zwagerman | Champaign, IL | 1:04:39 |
| 2013 | Abbey Bubolz | Manitowoc, WI | 1:08:54 |
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