| 1944 | None |
| 1945 | None |
| 1946 | None |
| 1947 | None (Entered Float - 1st Place) |
| 1948* | Don Wustenberg |
| 1949 | Jim Davis |
| 1950 | H. Scheirenberg "The Shadow" |
| 1951 | "Double Barrow" Carrow |
| 1952 | Clark Lane "Fargo Kid" |
| 1953 | Bud Barrett (Buckboards) |
| 1954 | Don "Rabbit" Young |
| 1955 | Moe Williams |
| 1956 | Bill Rich |
| 1957 | Bill "Apache" Bledsoe |
| 1958 | Bert Wittaker "Diamond Red" |
| 1959 | Dave Hitchcock "Dakota" |
| 1960* | Jerry "JayHawk" Willis |
| 1961 | Ed "Okark" Kimball (Mountain Men) |
| 1962 | Wayne Tarr (El Libre) |
| 1963* | "Mighty" Mike Kelly (Loggers) |
| 1964 | Dave "Smoke" Stathem (Firemen) |
| 1965* | Mike Freese (Whalers) |
| 1966 | Lani "Wildcat" Waller (Oilers) |
| 1967 | Dan Smith (Red Baron) |
| 1968 | Bob Tobias (Wine Merchants) |
| 1969 | John D'Anna (Lifeguards) |
| 1970 | Bill McKinney (Tanners) |
| 1971* | Rob Newell (Whalers) |
| 1972 | Steve Mendoza (Mexican Banditos) |
| 1973 | Big Chuck Seufferlein (Rugby) |
| 1974 | Tom Riehl (Goldminers) |
| 1975 | None |
| 1976 | Steve Alberti (Moon Cussers) |
| 1977 | Bambi May (Texas Rangers) |
| 1978 | Rocky Kemp (Fishpackers) |
| 1979 | Alfonso Carmona (Reinfield Imports) |
| 1980 | Andy Scultz (Sgt. York & Doughboys) |
| 1981 | Jim Harvey (Adolf Coors) |
| 1982 | Dan Keifer (Henry Ford) |
| 1983 | Andy "Dawg" Weinrich (Surfers) |
| 1984 | "Bad" Brad Magers (U.S. Marines) |
| 1985 | Craig Boschi (Bell Telephone) |
| 1986 | Mike Goodman (Benny Goodman) |
| 1987 | Mike Imelio (General Guadalupe Vallejo) |
| ( ) | = Pioneer Days Theme |
| * | = Elected Sheriff |
Pioneer Days was cancelled in the Spring of 1987. It returned briefly as "Rancho Chico Days," only to be cancelled again due to riots caused by out of town guests who were invited by MTV and Playboy Magazine.
