| Year | Winner | Location |
|---|---|---|
| 1973 | James H. Morgan Pilot Freight Carriers North Carolina | Denver, CO |
| 1976 | Bruce H. Lekson Midwest Motor Express, Inc. Minnesota | Fort Worth, TX |
| 1977 | Bruce H. Lekson Midwest Motor Express, Inc. Minnesota | Kansas City, MO |
| 1978 | William J. Purdy Consolidated Freightways New York | St. Louis, MO |
| 1979 | Tito Carrero Suburban Motor Freight, Inc. Oak Forest, IL | Phoenix, AZ |
| 1980 | Hershel W. Barnett Smiser Freight Service Southgate, CA | Kansas City, MO |
| 1981 | George P. Holik Eazor Express, Inc. Illinois | Indianapolis, IN |
| 1982 | James R. Hansen Milwaukee Motor Transportation Wood Dale, IL | Kansas City, MO |
| 1983 | George P. Holik Steve J. Dunne Cartage Co. Chicago, IL | Fort Worth, TX |
| 1984 | Lawrence Raison P & C Food Markets, Inc. New York | Indianapolis, IN |
| 1985 | Joseph E. Toth Rim Rock Trucking Inc. Staten Island, NY | St. Louis, MO |
| 1986 | Pete F. Angrick Yellow Freight System Indiana | Kansas City, MO |
| 1987 | Bruce W. Wells Milwaukee Motor Transportation Arlington Heights, IL | Fort Worth, TX |
| 1988 | Robert W. Taylor Robinson Terminal District of Columbia | St. Louis, MO |
| 1989 | Ronald J. Bowman, Sr. Getty Petroleum Corp. Aladan, PA | Memphis, TN |
| 1990 | Richard Gillespie Star Tribune Newspaper Minneapolis, MN | Dallas, TX |
| 1991 | Douglas S. Banicki Advance Transportation Illinois | Minneapolis, MN |
| 1992 | Joseph Toth Rimrock Trucking Inc. New York | Nashville, TN |
| 1993 | Mark A. Leatherwood Imperial Sweetner Texas | Denver, CO |
| 1994 | Ronald J. Bowman, Sr. Getty Petroleum Corp. New Jersey | Tampa, FL |
| 1995 | Mark Corriveau Hannaford Trucking Company Maine | New Orleans, LA |
| 1996 | Lawrence W Raison P & C Food Markets New York | Columbus, OH |
| 1997 | Lawrence W Raison P & C Food Markets New York | Minneapolis, MN |
| 1998 | Michael S. Hanson Sysco Food Services Minnesota | Long Beach, CA |
| 1999 | Robert N. Brown Jag Trux Pennsylvania | Tampa, FL |
| 2000 | Rick Craig Caylor Wal-Mart Stores, Inc. Colorado | New Orleans, LA |
| 2001 | Mike S. Hanson Sysco Food Services Minnesota | Minneapolis, MN |
| 2002 | John Roberts Publix Supermarkets Florida | Milwaukee, WI |
| 2003 | James L. Bryan FedEx Freight California | Columbus, OH |
| 2004 | Richard W. Crowder FedEx Freight Kentucky | Salt Lake City, UT |
| 2005 | Mark Church Con-Way Southern Express North Carolina | Tampa, FL |
| 2006 | Anthony Spero ABF Freight System, Inc. Connecticut | New Orleans, LA |
| 2007 | John A. Smith, Jr. FedEx Ground Mississippi | Minneapolis, MN |
| 2007 | Brian E. Walker FedEx Freight Colorado | Minneapolis, MN |
| 2008 | Ben S. Moore, Jr. Wal-Mart Transportation, LLC Georgia | Houston, TX |
| 2009 | Warren M. "Mick" Simpson Family Dollar Trucking North Carolina | Pittsburgh, PA |
| 2010 | John A. Smith, Jr. FedEx Ground Mississippi | Columbus, OH |
| 2011 | Edward A. Hawkins Leavitt's Freight Service Oregon | Orlando, FL |
| 2012 | Donald R. Logan FedEx Freight Kansas | Minneapolis, MN |
| 2013 | Richard W. Crowder FedEx Freight Kentucky | Salt Lake City, UT |
| 2014 | Paul Brandon FedEx Freight Connecticut | Pittsburgh, PA |
| 2015 | Scott Woodrome FedEx Freight Ohio | St. Louis, MO |
| 2016 | Jay Love FedEx Freight South Dakota | Indianapolis, IN |
| 2017 | Richard W. Crowder FedEx Freight Kentucky | Orlando, FL |
| 2018 | Steven Newsome UPS Freight South Carolina | Columbus, OH |
| 2019 | Basher Pierce FedEx Freight North Carolina | Pittsburgh, PA |
| 2022 | Eric Ramsdell Walmart Transportation, LLC Arizona | Indianapolis, IN |
| 2023 | Daryl Miller The Cope Company Salt Pennsylvannia | Columbus, OH |
| 2024 | Rueben Cortez H-E-B Grocery Co. Texas | Indianapolis, IN |
| 2025 | Edward Hill FedEx Freight Delaware | Minneapolis, MN |
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