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| Year | Athlete | School | Time |
| 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 |