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| Year | Class 4A | School | Time | Class 3A | School | Time |
| 2025 | Jase Burton | Star Valley | 4:12.01 | Trajn Swalstad | Worland | 4:35.59 |
| 2024 | Micah Colling | Kelly Walsh | 4:30.57 | Habtamu Wetzel | Star Valley | 4:23.75 |
| 2023 | Jackson Dutcher | Natrona | 4:29.10 | Owen Burnett | Mountain View | 4:21.70 |
| 2022 | Austin Akers | Sheridan | 4:33.32 | | | |
| 2021 | Peter Visser | Star Valley | 4:14.81 | | | |
| 2020 | Peter Visser | Star Valley | 4:31.72 | | | |
| 2019 | Asefa Wetzel | Star Valley | 4:22.88 | | | |
| 2018 | Shane Henderson | Cheyenne South | 4:29.22 | | | |
| 2017 | Shane Henderson | Star Valley | 4:29.13 | | | |
| 2016 | Brody Smith | Cody | 4:15.12 | | | |
| 2015 | Hunter Davila | Kelly Walsh | 4:25.33 | | | |
| 2014 | Ricky Faure | Rock Springs | 4:15.14 | | | |
| 2013 | Ricky Faure | Rock Springs | 4:18.98 | | | |
| 2012 | Ricky Faure | Rock Springs | 4:31.94 | | | |
| 2011 | Dylan Morin | Sheridan | 4:25.10 | | | |
| 2010 | Garrett Zans | Rock Springs | 4:34.86 | | | |
| 2009 | Dominick Robinson | Campbell County | 4:37.86 | | | |
| 2008 | Austin Huff | Cheyenne East | 4:43.87 | | | |
| 2007 | Taylor Kelting | Campbell County | 4:32.22 | | | |
| 2006 | Taylor Kelting | Campbell County | 4:42.66 | | | |