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| Year | Class 4A | School | Time | Class 3A | School | Time |
| 2024 | Bridger Brokaw | Cheyenne Central | 1:58.03 | Charlie Hulbert | Cody | 1:57.24 |
| 2023 | Jackson Dutcher | Natrona | 1:57.51 | Colby Jenks | Pinedale | 1:53.92 |
| 2022 | Kyland Fuller | Torrington | 2:01.11 | | | |
| 2021 | Kyland Fuller | Torrington | 2:03.17 | | | |
| 2020 | Peter Visser | Star Valley | 1:58.24 | | | |
| 2019 | Asefa Wetzel | Star Valley | 1:57.73 | | | |
| 2018 | Wyatt Peck | Star Valley | 1:55.00 | | | |
| 2017 | Cory Myers | Campbell County | 1:57.66 | | | |
| 2016 | Elliott Miller | Cheyenne Central | 1:58.13 | | | |
| 2015 | Hunter Davila | Kelly Walsh | 1:59.13 | | | |
| 2014 | Hunter Davila | Kelly Walsh | 1:54.64 | | | |
| 2013 | Ricky Faure | Rock Springs | 1:54.25 | | | |
| 2012 | Ricky Faure | Rock Springs | 1:58.93 | | | |
| 2011 | Dylan Morin | Sheridan | 2:00.22 | | | |
| 2010 | Cody Francom | Green River | 2:01.89 | | | |
| 2009 | Dominick Robinson | Campbell County | 2:02.57 | | | |
| 2008 | Ethan Slight | Cody | 2:07.67 | | | |
| 2007 | Matt Carey | Cheyenne Central | 2:06.14 | | | |
| 2006 | Bob Hewitt-Gaffney | Campbell County | 2:05.98 | | | |