| Year | Winner | Location |
|---|---|---|
| 1940 | Orville Hoffert Transamerican Freight Lines Indianapolis, IN | Chicago, IL |
| 1941 | Charles Goins Trucking Inc. Indianapolis, IN | New York, NY |
| 1946 | Charles Goins Trucking Inc. Indianapolis, IN | Chicago, IL |
| 1947 | Alex Adamski Geo. H. Alger Co. Chicago, IL | Los Angeles, CA |
| 1948 | Thomas Bennane Trucking Inc. Detroit, MI | Washington, D.C. |
| 1949 | S.L. Moon Georgia Highway Express Atlanta, GA | Boston, MA |
| 1950 | Richard Wold Glenndenning Motorways Minnesota | New York, NY |
| 1951 | James E. Tucker Great Southern Trucking Inc. Charlotte, NC | Chicago, IL |
| 1952 | Perry H. Reid Pilot Freight Carriers Winston-Salem, NC | New York, NY |
| 1953 | Perry H. Reid Pilot Freight Carriers Winston-Salem, NC | Minneapolis, MN |
| 1954 | Aubrey L. Harper Super Service Motor Frt. Co. Chattanooga, TN | Los Angeles, CA |
| 1955 | Aubrey L. Harper Super Service Motor Frt. Co. Chattanooga, TN | Washington, D.C. |
| 1956 | Leeland H. Hellestad Express Freight Lines Milwaukee, WI | New York, NY |
| 1957 | Aubrey L. Harper Super Service Motor Frt. Co. Chattanooga, TN | Chicago, IL |
| 1958 | Leo W. Ford Pilot Freight Carriers, Inc. Winston-Salem, NC | Miami Beach, FL |
| 1959 | Leo W. Ford Pilot Freight Carriers, Inc. Winston-Salem, NC | Louisville, KY |
| 1960 | Leeland H. Hellestad Express Freight Lines Milwaukee, WI | St. Paul, MN |
| 1961 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Detroit, MN |
| 1962 | Harry R. Wooten, Jr. Hennis Freight Lines Roanoke, VA | Dallas, TX |
| 1963 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Miami Beach, FL |
| 1964 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Louisville, KY |
| 1965 | Edward S. Schneider Olson Transportation Co. Fond de Lac, WI | Kansas City, MO |
| 1966 | William J. Long Lyons Transportation Lines Richfield, OH | Minneapolis, MN |
| 1967 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Tulsa, OK |
| 1968 | Ben C. Spain Mason & Dixon Lines, Inc. New Jersey | Cincinnati, OH |
| 1969 | Eugene Grubb, Sr. Roadway Express, Inc. Ohio | Denver, CO |
| 1970 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Miami Beach, FL |
| 1971 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Houston, TX |
| 1972 | Claude A. Pollett Mason & Dixon Lines, Inc. New York | Louisville, KY |
| 1973 | Richard A. Gillespie Century-Mercury Motor Freight Minnesota | Denver, CO |
| 1974 | William M. Schmidt Ryder Truck Lines, Inc. | Minneapolis, MN |
| 1975 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Indianapolis, IN |
| 1976 | Cletus C. Frank Akers Motor Lines Greensboro, NC | Fort Worth, TX |
| 1977 | Joseph L. Wilcock Milne Truck Lines, Inc. Utah | Kansas City, MO |
| 1978 | D. Page Robbins The Mason & Dixon Lines, Inc. North Carolina | St. Louis, MO |
| 1979 | Jesse L. Stauffer A-P-A Transport Lancaster, PA | Phoenix, AZ |
| 1980 | Lyle R. Gruntorad Graves Truck Lines Lincoln, NE | Kansas City, MO |
| 1981 | George DeMartini A-P-A Transport Corp. New Jersey | Indianapolis, IN |
| 1982 | George DeMartini A-P-A Transport Corp. New Jersey | Kansas City, MO |
| 1983 | Melvine Yoon Choy Kahele Gasco, Inc. Honolulu, HI | Fort Worth, Tx |
| 1984 | Lyle Gruntorad ANR Freight System Nebraska | Indianapolis, IN |
| 1985 | Jesse L. Stauffer A-P-A Transport Lancaster, PA | St. Louis, MO |
| 1986 | Jesse L. Stauffer A-P-A Transport Lancaster, PA | Kansas City, MO |
| 1987 | Les Beall Safeway Stores Bowie, MD (Representing DC) | Fort Worth, TX |
| 1988 | Patrick A. Engle Quast Transfer, Inc. Minnesota | St. Louis, MO |
| 1989 | Charles S. Goodrich Overnite Transportation Richmond, VA | Memphis, TN |
| 1990 | Robert Dolan A-P-A Transport Corp. Pennsylvania | Dallas, TX |
| 1991 | Larry Steadman Bryan Foods Mississippi | Minneapolis, MN |
| 1992 | Daniel Slonekar Beckman Produce Minnesota | Nashville, TN |
| 1993 | Wm. "Bubba" Fiveash Tom Thumb Stores Texas | Denver, CO |
| 1994 | Stephan Plonski J.P. Food Service Minnesota | Tampa, FL |
| 1995 | James Denny CF Motor Freight Minnesota | New Orleans, LA |
| 1996 | Bart L. Kooyman Food Services of America Washington | Columbus, OH |
| 1997 | Joe G. Gonzalez H.E.B. Grocery Company Texas | Minneapolis, MN |
| 1998 | Dale E. Andersen Crouse Cartage Company Iowa | Long Beach, CA |
| 1999 | Robert J. Dolan A-P-A Transport Corp Pennsylvania | Tampa, FL |
| 2000 | Kenneth R. Epley Roadway Express, Inc. Illinois | New Orleans, LA |
| 2001 | Daniel T. Poole Boeing Company Washington | Minneapolis, MN |
| 2002 | David C. Murphy Yellow Transportation, Inc. New Hampshire | Milwaukee, WI |
| 2003 | Mark S. Dietsche FedEx Freight Oregon | Columbus, OH |
| 2004 | James E. Carver Collington Services, LLC Maryland | Salt Lake City, UT |
| 2005 | Robert Dolan A-P-A Transport Corp. Pennsylvania | Tampa, FL |
| 2006 | Randy Devault Roadway Maine | New Orleans, LA |
| 2007 | Scott B. Watts FedEx Express Alaska | Minneapolis, MN |
| 2008 | Dennis R. Shirar Heritage Transport, LLC Indiana | Houston, TX |
| 2009 | Robert J. Dolan Con-way Freight Pennsylvania | Pittsburgh, PA |
| 2010 | Scott B. Watts FedEx Express Alaska | Columbus, OH |
| 2011 | Paul J. Phillips Con-way Freight California | Orlando, FL |
| 2012 | Robert J. Dolan Con-way Freight Pennsylvania | Minneapolis, MN |
| 2013 | James E. Carver Collington Services, LLC Maryland | Salt Lake City, UT |
| 2014 | Brendan Sharp FedEx Freight Colorado | Pittsburgh, PA |
| 2015 | Jeremy Steger Con-way Freight Wisconsin | St. Louis MO |
| 2016 | Charles Randolph Pitt Ohio West Virginia | Indianapolis, IN |
| 2017 | Richard Bailey FedEx Freight Michigan | Orlando, FL |
| 2018 | Dale Brenaman UPS Kentucky | Columbus, OH |
| 2019 | Jason Imhoff Walmart Transportation Ohio | Pittsburgh, PA |
| 2022 | Christopher Shaw FedEx Express New Mexico | Indianapolis, IN |
| 2023 | David Coffel FedEx Express Arizona | Columbus, OH |
| 2024 | James Kohr FedEx New York | Indianapolis, IN |
| 2025 | Mark Carver FedEx Freight Missouri | Minneapolis, MN |
