| Year | Winner | Location |
|---|---|---|
| 1957 | James A. Davis Chippewa Motor Freight Illinois | Chicago, IL |
| 1958 | Floyd F. Brown Motor Cargo, Inc. Milwaukee, WI | Miami Beach, FL |
| 1959 | Floyd F. Brown Motor Cargo, Inc. Milwaukee, WI | Louisville, KY |
| 1960 | Donald J Beaudette Land O'Lakes Creameries, Inc. Minneapolis, MN | St. Paul, MN |
| 1961 | Arnold C. Alcorn Standard Oil Division of Amoco Golden Valley, MN | Detroit, MI |
| 1962 | William J. Kline Mason & Dixon Lines, Inc. Philadelphia, PA | Dallas, TX |
| 1963 | Clyde W. Lutz Carolina Freight Carriers Corp. Carryville, NC | Miami Beach, FL |
| 1964 | Clyde W. Lutz Carolina Freight Carriers Corp. Carryville, NC | Louisville, KY |
| 1965 | Donald J Beaudette Land O'Lakes Creameries, Inc. Minneapolis, MN | Kansas City, MO |
| 1966 | Teddy A. Green Mason & Dixon Lines, Inc. | Minneapolis, MN |
| 1967 | Richard Wilke Mason & Dixon Lines, Inc. New Jersey | Tulsa, OK |
| 1968 | William J. Long Lyons Transportation Lines, Inc. Ohio | Cincinnati, OH |
| 1969 | Norman L. Reel Crouch Bros. Kansas | Denver, CO |
| 1970 | Paul D. Good Suburban Motor Freight Ohio | Miami Beach, FL |
| 1971 | William J. Klein Mason & Dixon Lines, Inc. Pennsylvania | Houston, TX |
| 1972 | George P. Holik Eazor Express, Inc. Illinois | Louisville, KY |
| 1973 | William J. Klein Mason & Dixon Lines, Inc. Pennsylvania | Denver, CO |
| 1974 | Ronald J Bowman, Sr. Getty Oil Co. Pennsylvania | Minneapolis, MN |
| 1975 | Glen D. Harris Chicago Kansas City Freight Line Kansas | Indianapolis, IN |
| 1976 | William J. Klein Mason & Dixon Lines, Inc. Pennsylvania | Fort Worth, TX |
| 1977 | Richard A. Gillespie Century-Mercury Motor Freight, Inc. Minnesota | Kansas City, MO |
| 1978 | Teddy A. Green Mason & Dixon Lines, Inc. Virginia | St. Louis, MO |
| 1979 | Robert E. Friend Advanced United Expressways St. Anthony, MN | Phoenix, AZ |
| 1980 | George Holik Eazor Express Forest View, IL | Kansas City, MO |
| 1981 | James Hansen The Milwaukee Motor Trans. Co. Illinois | Indianapolis, IN |
| 1982 | Leonard E. Huffman Overnite Transportation Co. Richmond, VA | Kansas City, MO |
| 1983 | Ralph O. Webster Schrivner, Inc. Oklahoma City, OK | Fort Worth, TX |
| 1984 | George P Holik Steve J. Dunne Cartage Illinois | Indianapolis, IN |
| 1985 | W. James Glennnon, Jr. The Kroger Company Speedway, IN | St. Louis, MO |
| 1986 | Marvin J. Rhoades Transus, Inc. Georgia | Kansas City, MO |
| 1987 | George P Holik Steve J. Dunne Cartage Illinois | Fort Worth, TX |
| 1988 | Clarence S. Jenkins, Jr. Overnite Transportation Co. West Virginia | St. Louis, MO |
| 1989 | James A. Herrmann Gateway Foods Onalaska, WI | Memphis, TN |
| 1990 | Albert McGee Exxon Co., U.S.A. Louisiana | Dallas, TX |
| 1991 | Clarence J. Hasbrook Super Value Stores Minnesota | Minneapolis, MN |
| 1992 | Mark Corriveau Hannaford Trucking Company Maine | Nashville, TN |
| 1993 | Charles C. Brown Pepsico Food Systems Kansas | Denver, CO |
| 1994 | Frederick H. Schenk DeMoulas Markets Massachusetts | Tampa, FL |
| 1995 | Domenick Santarcangelo Martin Brower Company Florida | New Orleans, LA |
| 1996 | Eleno P. Lara H.E.B. Grocery Texas | Columbus, OH |
| 1997 | Horace A Davis, Jr. Wal-Mart Stores, Inc. Texas | Minneapolis, MN |
| 1998 | Jason K. Frey Overnight Transportation Co. Massachusetts | Long Beach, CA |
| 1999 | Eleno P. Lara H.E.B. Grocery Texas | Tampa, FL |
| 2000 | Tom C. Turner Martin Brower Co., Inc. Georgia | New Orleans, LA |
| 2001 | Joseph E. Obregon Ruan Transp. Management Systems Georgia | Minneapolis, MN |
| 2002 | John R. Plummer Wal-Mart Transportation, LLC New Hampshire | Milwaukee, WI |
| 2003 | Scott Stoudnour Jevic Transportation, Inc. Pennsylvania | Columbus, OH |
| 2004 | Toby Kort FedEx Freight Nebraska | Salt Lake City, UT |
| 2005 | Ryland Hogan Wilson Trucking Corporation Virginia | Tampa, FL |
| 2006 | James Hines Wal-Mart Transportation, LLC Virginia | New Orleans, LA |
| 2007 | Kevin S. Harris, Sr. ABF Freight System, Inc. New York | Minneapolis, MN |
| 2008 | Buner H. Evans USF Holland Georgia | Houston, TX |
| 2009 | Dale L. Duncan Con-Way Freight California | Pittsburgh, PA |
| 2010 | Steve M. Elliston Wal-Mart Transportation, LLC Michigan | Columbus, OH |
| 2011 | Hershel B. Evans Holland Georgia | Orlando, FL |
| 2012 | Michael C. Grogan Con-Way Freight Idaho | Minneapolis, MN |
| 2013 | George D. Johnson UPS Freight Virginia | Salt Lake City, UT |
| 2014 | Wayne Gootee Walmart Transportation, LLC Michigan | Pittsburgh, PA |
| 2015 | Eric Ramsdell Walmart Transportation Oregon | St. Louis, MO |
| 2016 | Toby Kort FedEx Freight Nebraska | Indianapolis, IN |
| 2017 | Michael Miltrnberger Pitt Ohio Maryland | Orlando, FL |
| 2018 | Duane Staveness FedEx Freight Wisconsin | Columbus, OH |
| 2019 | David Hall ABF Freight Arkansas | Pittsburgh, PA |
| 2022 | David Guinn Publix Super Markets, Inc. Florida | Indianapolis, IN |
| 2023 | John Greene FedEx Freight Connecticut | Columbus, OH |
| 2024 | Brandon Hardy XPO Nevada | Indianapolis, IN |
| 2025 | David Comings FedEx Freight North Dakota | Minneapolis, MN |
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