| Year | Class 4A/AA | School | Time | Class 3A/A | School | Time | |
|---|---|---|---|---|---|---|---|
| 2025 | Colin Gilmore | Green River | 47.47 | Finn Richards | Lander | 46.07 | |
| 2024 | Gunner Seiloff | Rock Springs | 48.39 | Benny Kulow | Lander | 47.22 | |
| 2023 | John Spicer | Rock Springs | 47.30 | Benny Kulow | Lander | 46.97 | |
| 2022 | John Spicer | Rock Springs | 48.25 | Jonny Kulow | Lander | 44.15 | |
| 2021 | Carter Mahoney | Kelly Walsh | 47.63 | Brennen Blackburn | Lander | 47.25 | |
| 2020 | Ian Pfaff | Kelly Walsh | 47.05 | Jonny Kulow | Lander | 45.36 | |
| 2019 | Gunnar Poley | Thunder Basin | 46.31 | Jonny Kulow | Lander | 46.43 | |
| 2018 | Oscar Patten | Sheridan | 47.13 | Zayne Cooper | Worland | 48.03 | |
| 2017 | Ty Conklin | Campbell County | 47.44 | Ryan Brinda | Lander | 49.71 | |
| 2016 | Jeremiah Young | Kelly Walsh | 46.18 | Griffin Leemon | Lander | 47.48 | |
| 2015 | Jeremy Young | Kelly Walsh | 46.61 | Griffin Leemon | Lander | 48.38 | |
| 2014 | Thomas Reams | Cheyenne Central | 46.81 | Connor Petty | Worland | 47.71 | |
| 2013 | Kyle White | Cheyenne Central | 44.99 | Symen Ooms | Worland | 47.94 | |
| 2012 | Garrett Koehler | Cheyenne Central | 47.23 | Connor Petty | Worland | 48.52 | |
| 2011 | Nick Dillinger | Campbell County | 45.06 | Nick Robinson | Lander | 48.28 | |
| 2010 | Garrett Koehler | Cheyenne Central | 48.10 | Alex Fowler | Lander | 48.86 | |
| 2009 | Nick Dillinger | Campbell County | 46.18 | Alex Robinson | Lander | 48.12 | |
| 2008 | Erik Heiss | Kelly Walsh | 47.70 | Riley Johnson | Kemmerer | 48.99 | |
| 2007 | Isak Nti-Asare | Laramie | 46.83 | Terry Rolfe | Buffalo | 49.08 | |
| 2006 | Isak Nti-Asare | Laramie | 46.75 | Terry Rolfe | Newcastle | 49.83 | |
| 2005 | Ben Turner | Laramie | 47.77 | Riley Johnson | Kemmerer | 50.21 | |
| 2004 | Scott Bruce | Campbell County | 47.83 | Dakotah Konicek | Lander | 50.12 | |
| 2003 | Danny Weeks | Green River | 48.67 | Jayson Millhouse | Buffalo | 49.56 | |
| 2002 | Justin VanBaalen | Laramie | 48.40 | Jayson Millhouse | Buffalo | 50.24 | |
| 2001 | Trevor Castillon | Green River | 47.53 | Beau Taylor | Lander | 49.76 | |
| 2000 | Zach Mueller | Laramie | 48.63 | Cameron Cook | Buffalo | 46.84 | |
| 1999 | Jon George | Natrona | 47.31 | Cameron Cook | Buffalo | 47.12 | |
| 1998 | Ben Britton | Green River | 48.02 | Jake Rehard | Rawlins | 46.03 | |
| 1997 | Jason Garman | Laramie | 46.68 | Jake Rehard | Rawlins | 46.07 | |
| 1996 | Justin Kapinus | Campbell County | 46.68 | Jake Rehard | Rawlins | 46.98 | |
| 1995 | Matt Strauss | Green River | 48.08 | Jake Rehard | Rawlins | 48.59 | |
| 1994 | Matt Strauss | Green River | 47.69 | Ryan Mikesell | Lander | 49.76 | |
| 1993 | Heber Richardson | Laramie | 46.79 | Ryan Rigg | Worland | 48.80 | |
| 1992 | Scott Nicolarsen | Campbell County | 46.64 | Ryan Rigg | Worland | 50.29 | |
| 1991 | Rob Kirk | Campbell County | 46.10 | Chris Morgan | Rawlins | 47.65 | |
| 1990 | Mickey McDill | Campbell County | 48.13 | Dustin Hockett | Buffalo | 48.96 | |
| 1989 | J.D. Gale | Campbell County | 49.07 | Dustin Hockett | Buffalo | 48.91 | |
| 1988 | Joe Gale | Campbell County | 49.76 | Dustin Hockett | Buffalo | 50.11 | |
| 1987 | Greg Anderson | Laramie | 48.61 | Greg Tesoro | Evanston | 48.40 | |
| 1986 | Jeff Shope | Lander | 48.70 | Greg Tesoro | Evanston | 49.76 | |
| 1985 | Joe Hess | Green River | 47.76 | Greg Tesoro | Evanston | 49.71 | |
| 1984 | Karl Moore | Laramie | 48.29 | Jim Wise | Douglas | 50.96 | |
| 1983 | Karl Moore | Laramie | 54.186 | Daleray Madewell | Douglas | 58.121 | **races in meters |
| 1982 | Rob Bress | Laramie | 48.208 | Glenn Eiden | Big Piney | 53.125 | |
| 1981 | Ken Crouse | Kelly Walsh | 49.288 | John Marx | Big Piney | 51.753 | |
| 1980 | Dan Brubaker | Lander | 55.069 | John Marx | Big Piney | 58.914 | **races in meters |
| 1979 | Kyle Moore | Laramie | 48.591 | Mike Barker | Newcastle | 58.877 | **Class A races in meters |
| 1978 | Dan Brubaker | Lander | 51.13 | Greg Saul | Glenrock | 58.768 | **Class A races in meters |
| 1977 | Rick Cook | Cody | 49.899 | Greg Saul | Glenrock | 53.398 | |
| 1976 | John Masek | Natrona | 50.26 | Glen Walker | Lyman | 52.14 | |
| 1975 | John Masek | Natrona | 49.57 | Mark Patceg | Thermopolis | 53.52 | |
| 1974 | Bruce Hicks | Powell | 51.00 | Bruce Roumell | Glenrock | 53.60 | |
| 1973 | Bruce Hicks | Powell | 51.4 | Bruce Roumell | Glenrock | 53.2 | |
| 1972 | Bruce Hicks | Powell | 52.8 | Mark Smith | Thermopolis | 53.9 | |
| 1971 | Ed Frye | Cheyenne East | 53.1 | Bruce Roumell | Glenrock | 54.9 | |
| 1970 | Richard Erie | Cheyenne Central | 52.4 | Mark Smith | Thermopolis | 56.9 | |
| 1969 | Richard Erie | Cheyenne Central | 52.0 | - | - | - | |
| 1968 | Ray Tollman | Powell | 52.5 | - | - | - | |
| 1967 | Ray Tollman | Powell | 52.3 | - | - | - | |
| 1966 | Myron Harrison | Rock Springs | 54.0 | - | - | - | |
| 1965 | Ray Brakke | Powell | 54.0 | - | - | - | |
| 1964 | Jim Betters | Powell | 56.4 | - | - | - | |
| 1963 | Jerry Tolman | Powell | ??? | - | - | - | |
| 1962 | Layne Kopischka | Powell | 55.4 | - | - | - | |
| 1961 | Layne Kopischka | Powell | 57.6 | - | - | - | |
| 1960 | Bill Woodard | Natrona | 56.6 | - | - | - | |
| 1959 | Ed Tolman | Powell | 59.5 | - | - | - | |
| 1958 | Bob Anderson | Cheyenne Central | 55.5 | - | - | - | |
| 1957 | Clint Summerfield | Cheyenne Central | 58.8 | - | - | - | |
| 1956 | Bob Riley | Natrona | 58.6 | - | - | - | |
| 1955 | Bill Riley | Natrona | 1:00.6 | - | - | - | |
| 1954 | Bill Nunn | Cheyenne Central | 1:03.0 | - | - | - | |
| 1953 | Meet canceled | - | - | - | |||
| 1952 | Wayne Brown | Cheyenne Central | 1:05.8 | - | - | - | |
| 1951 | John Moore | Cheyenne Central | 1:02.3 | - | - | - | |
| 1950 | Ronnie Brown | Cheyenne Central | 1:04.4 | - | - | - | |
| 1949 | Harold Hutton | Cheyenne Central | 1:04.4 | - | - | - | |
| 1948 | Harold Spargur | Natrona | 1:01.6 | - | - | - |