 |
| Year | Kings | Queens |
| 1900 | Charles Noe | |
| 1933-35 | Hairbreadth Harry | |
| 1936 | Scoop Shovel Scotty | |
| 1937-38 | King David I | |
| 1939 | Scoop Shovel Scotty | |
| 1940-45 | Hobo Ben Benson | |
| 1946 | Skeet Simmons | Polly Ellen Pep |
| 1947 | Hiway Johnny Weaver | Polly Ellen Pep |
| 1948 | Hobo Ben Benson | Polly Ellen Pep |
| 1949 | Cannonball Eddie | Box Car Myrtle |
| 1950 | Hobo Ben Benson | Box Car Myrtle |
| 1951 | Cannonball Eddie | Sylvia Davis |
| 1952 | Scoop Shovel Scotty | Sylvia Davis |
| 1953 | Hobo Ben Benson | Sylvia Davis |
| 1954-55 | Scoop Shovel Scotty | Box Car Betty Link |
| 1956 | Hobo Ben Benson | |
| 1957 | Scoop Shovel Scotty | |
| 1958 | Arizona Bill | Box Car Betty Link |
| 1959 | Scoop Shovel Scotty | |
| 1960-61 | King David I | Box Car Betty Link |
| 1962 | Scoop Shovel Scotty | |
| 1963 | Pennsylvania Kid Wilson | |
| 1964 | Beef Steak Charlie | |
| 1965 | Hard Rock Kid | |
| 1966 | Pennsylvania Kid | |
| 1967 | Hard Rock Kid | |
| 1968 | Pennsylvania Kid | |
| 1969 | Slow Motion Shorty | Box Car Myrtle |
| 1970 | Hard Rock Kid | Longlooker Mic |
| 1971 | Pennsylvania Kid | Longlooker Mic |
| 1972 | Hard Rock Kid | Longlooker Mic |
| 1973 | Steamtrain Maury | Longlooker Mic |
| 1974 | Slow Motion Shorty | Longlooker Mic |
| 1975 | Hard Rock Kid | Adventurer Jan |
| 1976 | Steamtrain Maury | LuAnn Uhden |
| 1977 | Sparky Smith | Longlooker Mic |
| 1978 | Steamtrain Maury | Longlooker Mic |
| 1979 | Steamtrain Maury | Longlooker Mic |
| 1980 | Sparky Smith | Cinderbox Cindy |
| 1981 | Steamtrain Maury | Hobo Lump |
| 1982 | Hobo Bill Mainer | Longlooker Mic |
| 1983 | Mountain Dew | Hobo Lump |
| 1984 | Fry Pan Jack | Slo Freight Ben |
| 1985 | Frisco Jack | Longlooker Mic |
| 1986 | Ramblin' Rudy | Minneapolis Jewel |
| 1987 | Alabama Hobo | Hobo Lump |
| 1988 | Fishbones | Would-be hobo |
| 1989 | El Paso Kid | Slo Freight Ben |
| 1990 | Songbird McCue | Gypsy Moon |
| 1991 | Ohio Ned | Minneapolis Jewel |
| 1992 | Roadhog USA | Connecticut Shorty |
| 1993 | Iowa Blackie | Blue Moon |
| 1994 | Sidedoor Pullman Kid | New York Maggie |
| 1995 | Luther the Jet Gett | Cinderbox Cindy |
| 1996 | Liberty Justice | Come On Pat |
| 1997 | Frog | Minneapolis Jewel |
| 1998 | New York Slim | Cinders |
| 1999 | Preacher Steve | Slo Freight Ben |
| 2000 | Bo Grump | M.A.D. Mary |
| 2001 | Grandpa Dudley | Derail |
| 2002 | Redbird Express | Nightingale |
| 2003 | Hobo Spike | Mama Joe |
| 2004 | Adman | Sunrise |
| 2005 | ???? | ???? |