| 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
2019 Slim Tim Flux (Magnolia)
2021 Buzzman Sully