| Year | Winner | Location |
|---|---|---|
| 1972 | James L. Rosel Peter's Truck Line California | Louisville, KY |
| 1973 | Roger L. Bailey Consolidated Freightways Utah | Denver, CO |
| 1974 | Henry F Fleishmann Consolidated Freightways Corp. Utah | Minneapolis, MN |
| 1975 | Robert L. Bailey Consolidated Freightways Corp. Utah | Indianapolis, IN |
| 1976 | Roger J. Hatch Advance United Expressways Minnesota | Fort Worth, TX |
| 1977 | Chester J. Radwan Neuendorf Transportation Illinois | Kansas City, MO |
| 1978 | Henry F Fleishmann Consolidated Freightways Utah | St. Louis, MO |
| 1979 | Henry F Fleishmann Consolidated Freightways Utah | Phoenix, AZ |
| 1980 | Tito Carrero Suburban Motor Freight, Inc. Oakforest, IL | Kansas City, MO |
| 1981 | Jack Hartman Consolidated Freightways Illinois | Indianapolis, IN |
| 1982 | Lowell Crouse Bulk Transport Service Shrewsbury, MA | Kansas City, MO |
| 1983 | William M. Whim Graves Truck Line, Inc. Kansas City, MO | Fort Worth, TX |
| 1984 | Robert L. White Idaho Delivery & Assembly Idaho | Indianapolis, IN |
| 1985 | Roger L. Lanham Overnite Transportation Charleston, WV | St. Louis, MO |
| 1986 | Eugene L. Langkand Consolidated Freightways Minnesota | Kansas City, MO |
| 1987 | Robert A. Wickboldt Peters Truck Lines Rocklin, CA | Fort Worth, TX |
| 1988 | Richard A. Gillespie Star Tribune Minnesota | St. Louis, MO |
| 1989 | Joel D. Johanneck Silver Eagle Company Sumner, WA | Memphis, TN |
| 1990 | Patrick Fulton Yellow Freight Systems Colorado | Dallas, TX |
| 1991 | Kenneth J. Heath Consolidated Freightways Utah | Minneapolis, MN |
| 1992 | Corky Shields CF Motor Freight Kansas | Nashville, TN |
| 1993 | Ryland B. Hogan Overnight Transportation Co. Virginia | Denver, CO |
| 1994 | Ted J. Hunger Viking Freight System, Inc. Colorado | Tampa, FL |
| 1995 | Kenneth Hawthorne, Jr. Overnight Transportation District of Columbia | New Orleans, LA |
| 1996 | John N Aranda Silver Eagle Oregon | Columbus, OH |
| 1997 | Anthony J. Cesenaro Overnight Transportation Co. Maryland | Minneapolis, MN |
| 1998 | Marty H. Lawson Harley-Davidson Transportation Pennsylvania | Long Beach, CA |
| 1999 | Michael Nardone RPS, Inc. Connecticut | Tampa, FL |
| 2000 | Keith Herzig FedEx Ground Connecticut | New Orleans, LA |
| 2001 | David G. McDonald Roadway Express, Inc. Kansas | Minneapolis, MN |
| 2002 | James March Yellow Transportation, Inc. Pennsylvania | Milwaukee, WI |
| 2003 | Merrit A. Oder FedEx Freight Kentucky | Columbus, OH |
| 2004 | Marty B. Hogan Overnight Transportation Virginia | Salt Lake City, UT |
| 2005 | Darrell Kimbrell FedEx Freight Alabama | Tampa, FL |
| 2006 | Robert French Con-Way Freight Virginia | New Orleans, LA |
| 2007 | Dennis Day Con-Way Freight Georgia | Minneapolis, MN |
| 2008 | Chris A. Mahony FedEx Freight Utah | Houston, TX |
| 2009 | Mark A. McLean FedEx Freight New York | Pittsburgh, PA |
| 2010 | Donald R. Logan FedEx Freight Kansas | Columbus, OH |
| 2011 | Jeffrey W. Payne Reddaway Utah | Orlando, FL |
| 2012 | Michael R. Umphrey Con-Way Freight Alabama | Minneapolis, MN |
| 2013 | Timothy W. Melody ABF Freight System, Inc. Idaho | Salt Lake City, UT |
| 2014 | Jeffrey Langenhahn Con-Way Freight Wisconsin | Pittsburgh, PA |
| 2015 | David Mogler FedEx Freight Colorado | St. Louis, MO |
| 2016 | Chris Poynor XPO Logistics Washington | Indianapolis, IN |
| 2017 | Chris Poynor XPO Logistics Washington | Orlando, FL |
| 2018 | Miguel Corral FedEx Freight Illinois | Columbus, OH |
| 2019 | Scott Woodrome FedEx Freight Ohio | Pittsburgh, PA |
| 2022 | Damien Hebert XPO Logistics, Inc. Louisiana | Indianapolis, IN |
| 2023 | Robert Fair FedEx Freight New Hampshire | Columbus, OH |
| 2024 | Conner Dent FedEx Freight Wisconsin | Indianapolis, IN |
| 2025 | Miguel Sanchez United Parcel Service, Inc. Florida | Minneapolis, MN |
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