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| Year | Class 4A | School | Time | Class 3A | School | Time |
| 2025 | Jase Burton | Star Valley | 9:04.64 | Trajn Swalstad | Worland | 9:56.22 |
| 2024 | Trevor Schmidt | Cheyenne Central | 9:47.06 | Habtamu Wetzel | Star Valley | 9:28.55 |
| 2023 | Tristan Enders | Natrona | 9:37.98 | Owen Burnett | Mountain View | 9:41.57 |
| 2022 | Jacob Frentheway | Cheyenne Central | 9:45.76 | | | |
| 2021 | Peter Visser | Star Valley | 9:57.09 | | | |
| 2020 | Peter Visser | Star Valley | 9:48.20 | | | |
| 2019 | Asefa Wetzel | Star Valley | 9:52.74 | | | |
| 2018 | Shane Henderson | Cheyenne South | 9:51.20 | | | |
| 2017 | Asefa Wetzel | Star Valley | 9:39.15 | | | |
| 2016 | Brody Smith | Cody | 9:20.59 | | | |
| 2015 | Brody Smith | Cody | 9:42.95 | | | |
| 2014 | Hunter Davila | Kelly Walsh | 9:30.77 | | | |
| 2013 | Hunter Davila | Kelly Walsh | 9:38.84 | | | |
| 2012 | Oliver Scofield | Star Valley | 9:52.40 | | | |
| 2011 | Dylan Morin | Sheridan | 9:38.63 | | | |
| 2010 | Garrett Zans | Rock Springs | 10:12.26 | | | |
| 2009 | Dominick Robinson | Campbell County | 10:23.99 | | | |
| 2008 | Laine Parish | Cheyenne Central | 10:04.09 | | | |
| 2007 | Taylor Kelting | Campbell County | 10:16.96 | | | |
| 2006 | Taylor Kelting | Campbell County | 10:32.05 | | | |