| Year |
King |
Queen |
| 1900 |
Charles Noe |
|
| 1933-35 |
Hairbreadth Harry |
|
| 1936 |
Scoop Shovel Scotty |
|
| 1937 |
King David II |
|
| 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 |
Scoop Shovel Scotty |
Box Car Betty Link |
| 1955 |
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 |
Box Car Betty Link |
| 1960 |
King David I |
|
| 1961 |
King David I |
|
| 1962 |
Scoop Shovel Scotty |
|
| 1963 |
Pennsylvania Kid Wilson |
|
| 1964 |
Beef Steak Charlie |
|
| 1965 |
Hardrock Kid |
|
| 1966 |
Pennsylvania Kid |
|
| 1967 |
Hardrock Kid |
|
| 1968 |
Pennsylvania Kid |
|
| 1969 |
Slow Motion Shorty |
Box Car Myrtle |
| 1970 |
Hardrock Kid |
Longlooker Mic |
| 1971 |
Pennsylvania Kid |
Longlooker Mic |
| 1972 |
Hardrock Kid |
Longlooker Mic |
| 1973 |
Steamtrain Maury |
Longlooker Mic |
| 1974 |
Slow Motion Shorty |
Longlooker Mic |
| 1975 |
Hardrock 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 Gette |
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 Jo |
| 2004 |
Adman |
Sunrise |
| 2005 |
Iron Horse Brad |
Half Track |
| 2006 |
Iowegian Rick |
Ms. Charlotte |
| 2007 |
Tuck |
Sonshine |
| 2008 |
Stretch |
Connecticut Tootsie |
| 2009 |
Inkman |
Stray Cat |
| 2010 |
Dante |
Double B |
| 2011 |
Uncle Freddie |
Minneapolis Jewel |
2012 Minnesota Jim Angel
2013 Frog Bookworm Bonnie
2014 Songbird Cindy Lou
2015 The Czech Hobo Hobo Lump
2016 Ricardo Sunrise
2017 Tuck Minneapolis Jewel
2018 Dutch Crash