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| Year | Class 4A/AA | School | Time | Class 3A/A | School | Time | Class 2A/B | School | Time | Class 1A/C | School | Time |
| 1979 | Tim Daniel | Riverton | 2:01.30 | not contested at A level | | | not contested at B level | | | Dale Harris | Kaycee | 2:07.00 |
| 1978 | Brian Ness | Cheyenne Central | 2:00.31 | Doug Manning | Thermopolis | 2:06.00 | Zane Straley | Pinedale | 2:06.20 | Truit Trowbridge | Encampment | 2:04.49 |
| 1977 | Mark Charkey | Cheyenne Central | 1:56.80 | Mark Hopp | Torrington | 2:00.11 | Dan Welch | Moorcroft | 2:04.92 | Kyle Hudson | Meeteetse | 2:08.00 |
| 1976 | Mark Charkey | Cheyenne Central | 1:57.69 | Tim Rainey | Star Valley | 2:03.00 | Zane Straley | Pinedale | 2:07.80 | Ferlin Harris | Kaycee | 2:10.20 |
| 1975 | Richard Bishop | Cheyenne East | 1:58.10 | Lex Madden | Lusk | 2:02.90 | Cubby Furlong | Wind River | 2:06.10 | Lyle Burgess | Encampment | 2:05.00 |
| 1974 | Donny Nichols | Laramie | 2:00.90 | Lex Madden | Lusk | 2:08.00 | Barney Brisko | Mountain View | 2:08.10 | Tom Peterson | Ten Sleep | 2:13.80 |
| 1973 | Ken Rieman | Lander | 2:03.1 | Paul Nelson | Torrington | 2:07.4 | Bob Hill | Lingle | 2:06.7 | Dale Fabricius | Burlington | 2:13.0 |
| 1972 | Rob Blacky | Riverton | 1:59.7 | Rick Kinnison | Buffalo | 2:04.4 | Robin Hibbard | Sundance | 2:03.8 | Jim Gomendi | Deaver-Frannie | 2:05.7 |
| 1971 | Rob Blacky | Riverton | 1:57.9 | Kevin Croft | Star Valley | 2:01.8 | Don Reynolds | Upton | 1:58.3 | Jim Gomendi | Deaver-Frannie | 2:04.6 |
| 1970 | Pat Dolan | Laramie | 2:01.1 | Kevin Croft | Star Valley | 2:03.4 | Don Reynolds | Upton | 1:59.1 | Jim Gomendi | Deaver-Frannie | 2:03.9 |
| 1969 | Jim Woodard | Cheyenne East | 1:56.8 | Randy Arp | Torrington | 2:06.1 | Don Reynolds | Upton | 2:01.5 | Jim Gomendi | Deaver-Frannie | 2:09.5 |
| 1968 | Dale Christensen | Natrona County | 2:00.1 | Mike Hladky | Campbell County | 2:03.3 | Mike Neville | Byron | 2:03.3 | Randy Emerson | Rock River | 2:09.3 |
| 1967 | Frank Wojtech | Kelly Walsh | 1:59.3 | Mike Hladky | Campbell County | 2:02.4 | Doug Pemberton | Big Piney | 2:03.3 | Larry Walker | Ten Sleep | 2:06.0 |
| 1966 | Frank Wojtech | Kelly Walsh | 2:01.1 | Bob Clark | Wheatland | 2:03.2 | Jim Gorman | Guernsey | 2:05.6 | Bill Dick | LaGrange | 2:08.0 |
| 1965 | Larry Wegmet | Powell | 2:06.6 | Frank Boyd | St. Stephens | 2:10.3 | Steven Asay | Byron | 2:10.4 | Don McKinney | Veteran | 2:16.6 |
| 1964 | Antonio Shakespeare | Lander | 2:04.5 | Pete Smith | St. Mary's | 2:04.0 | Leon Jay | Hulett | 2:02.4 | Arlie Ferguson | Hawk Springs | 2:11.2 |
| 1963 | Gary Goodman | Torrington | 2:02.5 | Harry Ashmead | Douglas | 2:05.2 | George Spoonhunter | St. Stephens | 2:03.6 | Bill Yeik | Yoder | 2:09.8 |
| 1962 | Gary Kopsa | Cheyenne East | 2:05.8 | Gary Goodman | Torrington | 2:07.6 | Leon Jay | Hulett | 2:09.4 | Bill Yeik | Yoder | 2:11.3 |
| 1961 | Gary Kopsa | Cheyenne East | 2:05.3 | Gary Goodman | Torrington | 2:10.6 | George Spoonhunter | St. Stephens | 2:07.5 | Wayne Thaler | LaGrange | 2:07.9 |
| 1960 | John O'Brien | Natrona County | 2:07.4 | Dean Johnson | Torrington | 2:01.0 | Dennis Smith | Basin | 2:03.0 | Wayne Thaler | LaGrange | 2:11.5 |
| 1959 | Ed Summerford | Natrona County | 2:09.1 | Dean Johnson | Torrington | 2:04.2 | Daniel Hart | Upton | 2:05.4 | Bruce Hattan | Veteran | 2:12.4 |
| 1958 | Gene Wright | Sheridan | 2:04.2 | Dean Johnson | Torrington | 2:06.8 | Daniel Hart | Upton | 2:09.1 | Gary Walden | Carpenter | 2:09.5 |
| 1957 | Chick Henn | Laramie | 2:12.4 | Carl Nelson | Rawlins | 2:03.9 | Jeff Haworth | Glenrock | 2:08.1 | Jim Hilbird | Rock River | 2:15.9 |
| 1956 | George Smith | Natrona County | 2:03.7 | Carl Nelson | Rawlins | 2:04.0 | Jeff Haworth | Glenrock | 2:12.1 | | | |
| 1955 | Joe Sims | Rock Springs | 2:11.0 | Lowell Bullock | Torrington | 2:06.6 | Jeff Haworth | Glenrock | 2:09.7 | | | |
| 1954 | George Smith | Natrona County | 2:03.6 | Lowell Bullock | Torrington | 2:00.815 | Don Weglin | Huntley | 2:14.7 | | | |
| 1953 | Don White | Cheyenne Central | 2:04.75 | Bill Wallace | St. Mary's | 2:08.6 | Gene Langwell | Veteran | 2:11.0 | | | |
| 1952 | Gary Eyre | Rawlins | 2:08.5 | Don Taylor | Green River | 2:12.2 | Ronald Koop | Upton | 2:10.2 | | | |
| 1951 | Gary Eyre | Rawlins | 1:59.7 | | | | Ronald Koop | Upton | 2:14.0 | | | |
| 1950 | Jerry Carroll | Powell | 2:07.7 | | | | | | | | | |
| 1949 | Dick Henderson | Natrona County | 2:10.0 | | | | | | | | | |
| 1948 | Richard Jons | Pine Bluffs | 2:11.3 | | | | | | | | | |
| 1947 | Bob Wallace | St. Mary's | 2:09.4 | | | | | | | | | |
| 1946 | Bill Sullenberger | Torrington | 2:15.3 | | | | | | | | | |
| 1945 | Ernie Davis | Natrona County | 2:16.2 | | | | | | | | | |
| 1944 | Jack Heron | Worland | 2:09.7 | | | | | | | | | |
| 1943 | No meet | - | - | | | | | | | | | |
| 1942 | Arthur Allen | Laramie | 2:16.4 | | | | | | | | | |
| 1941 | Dennis Rogers | Douglas | 2:10.0 | | | | | | | | | |
| 1940 | Dick Rowles | Laramie | 2:06.0 | | | | | | | | | |
| 1939 | Warren Garst | Douglas | 2:06.9 | | | | | | | | | |
| 1938 | Warren Garst | Douglas | 2:06.6 | | | | | | | | | |
| 1937 | Edward King | Rock Springs | 2:08.1 | | | | | | | | | |
| 1936 | Edward King | Rock Springs | 2:09.5 | | | | | | | | | |
| 1935 | Edelle Pirtle | Green River | 2:09.5 | | | | | | | | | |
| 1934 | Tim Cox | Albin | 2:10.2 | | | | | | | | | |
| 1933 | Tom Teesdale | Natrona County | 2:05.1 | | | | | | | | | |
| 1932 | Tom Teesdale | Natrona County | 2:04.1 | | | | | | | | | |
| 1931 | Emil Rohlff | Douglas | 2:10.3 | | | | | | | | | |
| 1930 | Tony Rulli | Sheridan | 2:16.0 | | | | | | | | | |
| 1929 | Emil Rohlff | Douglas | 2:10.4 | | | | | | | | | |
| 1928 | George Clark | Natrona County | 2:07.3 | | | | | | | | | |
| 1927 | George Clark | Natrona County | 2:12.4 | | | | | | | | | |
| 1926 | Harold Thatcher | Douglas | 2:06.8 | | | | | | | | | |
| 1925 | Creswell Northrup | Powell | 2:12.0 | | | | | | | | | |
| 1924 | George Gobel | Natrona County | 2:09.4 | | | | | | | | | |
| 1923 | Walter Smith | Greybull | 2:13.0 | | | | | | | | | |
| 1922 | Robert Porter | Parkerton | 2:19.4 | | | | | | | | | |