| Year | Class 4A/AA | School | Time |
|---|---|---|---|
| 1934 | Owen McGill | Wheatland | 27.4 |
| 1933 | Bill Gentle | Douglas | 26.2 |
| 1932 | Ed Hetland | Midwest | 27.4 |
| 1931 | Hale Brundage | Cody | 27.2 |
| 1930 | Francis Montague | Lusk | 27.09 |
| 1929 | Taft Harris | Natrona County | 26.9 |
| 1928 | Walt Dowler | Natrona County | 27.0 |
| 1927 | Taft Harris | Natrona County | 26.7 |
| 1926 | Blake Fanning | Laramie | 27.5 |
| 1925 | Ray Thompson//Eldon Penfield | Thermopolis//Thermopolis | 27.1 |
| 1924 | Ray Thompson | Thermopolis | 26.8 |
| 1923 | Ray Thompson | Thermopolis | 27.2 |
| 1922 | Orba Teninty | Thermopolis | 27.2 |