| Year | Winner | Location |
|---|---|---|
| 1997 | James P Hines Wal-Mart Stores Inc. Virginia | Minneapolis, MN |
| 1998 | James P Hines Wal-Mart Stores Inc. Virginia | Long Beach, CA |
| 1999 | Marty H. Lawson Harley-Davidson Transportation Pennsylvania | Tampa, FL |
| 2000 | David James Con-Way Central Express Illinois | New Orleans, LA |
| 2001 | Ricky D. Pledger Wal-Mart Stores, Inc. Texas | Minneapolis, MN |
| 2002 | Ben S. Moore, Jr. Wal-Mart Transportation, LLC Georgia | Milwaukee, WI |
| 2003 | Mark A. Taylor Wal-Mart Transportation, LLC California | Columbus, OH |
| 2004 | Teddy I. Abshire Overnight Transportation Ohio | Salt Lake City, UT |
| 2005 | Larry Warr Wal-Mart Transportation, LLC Georgia | Tampa, FL |
| 2006 | Rylans Hogan Wilson Trucking Corporation Virginia | New Orleans, LA |
| 2007 | Warren Lewis, Jr. Hannaford Trucking Company Maine | Minneapolis, MN |
| 2008 | Karl R. Bohrer Wal-Mart Transportation, LLC Texas | Houston, TX |
| 2009 | Troy J. Swenson FedEx Freight South Dakota | Pittsburgh, PA |
| 2010 | Bruce J. Quaal YRC Minnesota | Columbus, OH |
| 2011 | Joshua B. Carr Walmart Transportation, LLC Oregon | Orlando, FL |
| 2012 | Leo R. Flack A. Duie Pyle, Inc. Pennsylvania | Minneapolis, MN |
| 2013 | Gary W. Harms Walmart Transportation, LLC Kansas | Salt Lake City, UT |
| 2014 | Matt Awbrey Walmart Transportation Georgia | Pittsburgh, PA |
| 2015 | Ronald Emenheiser Walmart Transportation Pennsylvania | St. Louis, MO |
| 2016 | Larry Breen Walmart Transportation, LLC Florida | Indianapolis, IN |
| 2017 | Roland G. Bolduc FedEx Express Massachusetts | Orlando, FL |
| 2018 | Artur Lesniowski FedEx Ground New Jersey | Columbus, OH |
| 2019 | Charles Mike White Walmart Transportation Indiana | Pittsburgh, PA |
| 2022 | Roland Bolduc FedEx Express Connecticut | Indianapolis, IN |
| 2023 | Roland Bolduc FedEx Express Connecticut | Columbus, OH |
| 2024 | Gregory Ryan Walmart Transportation, LLC Arizona | Indianapolis, IN |
| 2025 | Merle Ashbaugh DHL Supply CHain Ohio | Minneapolis, MN |
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