| Year | Winner | Location |
|---|---|---|
| 1957 | William J. Klein The Mason & Dixon Lines, Inc. Pennsylvania | Chicago, IL |
| 1958 | Robert E. Rudesill Glendenning Motorways, Inc. St. Paul, MN | Miami Beach, FL |
| 1959 | Jesse E. Albright City Express, Inc. Maryland | Louisville, KY |
| 1960 | Jesse E. Albright City Express, Inc. Maryland | St. Paul, MN |
| 1961 | William J. Klein The Mason & Dixon Lines, Inc. Philadelphia, PA | Detroit, MI |
| 1962 | Peter G. Granello The Mason & Dixon Lines, Inc. New York City, NY | Dallas, TX |
| 1963 | Paul D. Goode Suburban Motor Freight, Inc. Columbus, OH | Miami Beach, FL |
| 1964 | Irvin J. Frey Branch Motor Express Company Reading, PA | Louisville, KY |
| 1965 | Bonnie A. Robison Southwestern Transportation Co. Memphis, TN | Kansas City, MO |
| 1966 | Peter G. Granello The Mason & Dixon Lines, Inc. New York City, NY | Minneapolis, MN |
| 1967 | Malcolm E. Thompson St. Johnsbury Trucking Co. Springfield, MA | Tulsa, OK |
| 1968 | Daniel Darnold Cook Motor Lines West Virginia | Cincinnati, OH |
| 1969 | George P. Holick Eazor Express Illinois | Denver, CO |
| 1970 | Peter G. Granello The Mason & Dixon Lines, Inc. New York City, NY | Miami Beach, FL |
| 1971 | William J. Long Lyons Transportation Lines Ohio | Houston, TX |
| 1972 | Earl H. Hudson Johnson Motor Lines, Inc. North Carolina | Louisville, KY |
| 1973 | Robert H. Gardener Pacific Intermountain Express Indiana | Denver, CO |
| 1974 | Daniel W. Darnold Cook Motor Lines West Virginia | Minneapolis, MN |
| 1975 | Robert D. Suck Cook Motor Lines, Inc. West Virginia | Indianapolis, IN |
| 1976 | Montie T. Webster Lee Way Motor Freight, Inc. Oklahoma | Fort Worth, TX |
| 1977 | David R. Gressley Consolidated Freightways Ohio | Kansas City, MO |
| 1978 | Gary L. Tunsky, Sr. Briggs Transportation Company Minnesota | St. Louis, MO |
| 1979 | Bruce Lekson Midwest Motor Express Minnesota | Phoenix, AZ |
| 1980 | Irvin F Eberly A-P-A Transport Lancaster, PA | Kansas City, MO |
| 1981 | Elwood Sherer Yellow Freight System Manheim, PA | Indianapolis, IN |
| 1982 | Elwood Sherer Yellow Freight System Manheim, PA | Kansas City, MO |
| 1983 | Leo A. Plumley American and Produce Co. Eagan, MN | Fort Worth, TX |
| 1984 | Richard A. Gillespie Century Motor Freight, Inc. Minnesota | Indianapolis, IN |
| 1985 | Robert E. Friend Advance United Expressways Anthony, MN | St. Louis, MO |
| 1986 | Jay H Mammau Yellow Freight System Pennsylvania | Kansas City, MO |
| 1987 | Dwight Adkins C W Transport, Inc. Charlotte, NC | Fort Worth, TX |
| 1988 | Craig A. Green Consolidated Freightways Idaho | St. Louis, MO |
| 1989 | Doyle L. Martin Safeway Stores, Inc. Alexandria, VA | Memphis, TN |
| 1990 | Chet Radwan Yellow Freight Systems Illinois | Dallas, TX |
| 1991 | Mr. J. Craig Bonds P. F. S. Colorado | Minneapolis, MN |
| 1992 | Raymond Simon Yellow Freight System, Inc. Minnesota | Nashville, TN |
| 1993 | Dana E. Moore Boeing Licensed Transp. Washington | Denver, CO |
| 1994 | Horace A Davis, Sr. Union Pacific Motor Freight Texas | Tampa, FL |
| 1995 | Edwin Jarzenski, Jr. ABF Freight System Ohio | New Orleans, LA |
| 1996 | Warren M. Simpson Family Dollar Trucking North Carolina | Columbus, OH |
| 1997 | Raymond Simon Yellow Freight System, Inc. Minnesota | Minneapolis, MN |
| 1998 | Everett S. Macmaster Jr. Federal Express Corporation Maine | Long Beach, CA |
| 1999 | Kenny D. Wulf Farmland Industries, Inc. Iowa | Tampa, FL |
| 2000 | Mark Dewain Ritter Wal-Mart Stores, Inc. South Carolina | New Orleans, LA |
| 2001 | Raymond Simon Yellow Freight System, Inc. Minnesota | Minneapolis, MN |
| 2002 | Larry Brenn Wal-Mart Transportation, LLC Florida | Milwaukee, WI |
| 2003 | Dale L. Duncan Con-Way Western Express Arizona | Columbus, OH |
| 2004 | Edward F. Romero Con-Way Western Express Arizona | Salt Lake City, UT |
| 2005 | Rick Hebert Yellow Transportation, Inc. Illinois | Tampa, FL |
| 2006 | Mark Hassemer Yellow Transportation, Inc. Wisconsin | New Orleans, LA |
| 2007 | Alphonso Lewis Roadway Alabama | Minneapolis, MN |
| 2008 | Ryan R. Kelley FedEx Freight Iowa | Houston, TX |
| 2009 | Michael W. Stickley Con-Way Freight Virginia | Pittsburgh, PA |
| 2010 | Jason D. Matte FedEx Freight Mississippi | Columbus, OH |
| 2011 | Gary W. Harms Walmart Transportation, LLC Kansas | Orlando, FL |
| 2012 | Scott A. Stroup YRC Freight Nebraska | Minneapolis, MN |
| 2013 | Ralph B. Garcia ABF Freight System, Inc. New Mexico | Salt Lake City, UT |
| 2014 | James Quarles Walmart Transportation, LLC South Carolina | Pittsburgh, PA |
| 2015 | Bradley Lester FedEx Freight Oregon | St. Louis, MO |
| 2016 | Ronald Metternick FedEx Freight Michigan | Indianapolis, IN |
| 2017 | James Duffy FedEx Freight Wisconsin | Orlando, FL |
| 2018 | Nick Arnold FedEx Freight Oklahoma | Columbus, OH |
| 2019 | Adam Heim FedEx Freight Idaho | Pittsburgh, PA |
| 2022 | Martin McMahon RIST Transport New York | Indianapolis, IN |
| 2023 | Martin McMahon RIST Transport New York | Columbus, OH |
| 2024 | Joseph Hicks XPO Rhode Island | Indianapolis, IN |
| 2025 | Stephen Johnson FedEx Freight Mississippi | Minneapolis, MN |
