| Year | Winner | Location |
|---|---|---|
| 1957 | Hubert L. Kennedy National Transit Corp. Cincinnati, OH | Chicago, IL |
| 1958 | Hubert L. Kennedy National Transit Corp. Cincinnati, OH | Miami Beach, FL |
| 1959 | Howard J. Pudliner Motor Cargo, Inc. Pennsylvania | Louisville, KY |
| 1960 | Walter F. Storm Davidson Transfer & Storage Co. Baltimore, MD | St. Paul, MN |
| 1961 | William G. Contres Mason & Dixon Lines, Inc. York, PA | Detroit, MI |
| 1962 | James W. Tilley Pilot Freight Carriers, Inc. Winston-Salem, NC | Dallas, TX |
| 1963 | Fred G. Staudt Mason & Dixon Lines, Inc. Secaucus, NJ | Miami Beach, FL |
| 1964 | William G. Contres Mason & Dixon Lines, Inc. York, PA | Louisville, KY |
| 1965 | Fred G. Staudt Mason & Dixon Lines, Inc. Secaucus, NJ | Kansas City, MO |
| 1966 | Rowland D. Mann B & L Motor Freight Newark, OH | Minneapolis, MN |
| 1967 | Edwin M. Smith Hennis Freight Lines, Inc. Durham, NC | Tulsa, OK |
| 1968 | Roy S. Southworth, Jr. Hennis Freight Lines Virginia | Cincinnati, OH |
| 1969 | Henry Fleischmann Consolidated Freightways Ohio | Denver, CO |
| 1970 | Marvin M. Harris Johnson Motor Lines, Inc. North Carolina | Miami Beach, FL |
| 1971 | Elton L. Lowry IML Freight, Inc. Missouri | Houston, TX |
| 1972 | Roy S. Southworth, Jr. Hennis Freight Lines Virginia | Louisville, KY |
| 1973 | George T. Bruss Chippewa Motor Freight, Inc. Illinois | Denver, CO |
| 1974 | George P. Holik Eazor Express, Inc. Illinois | Minneapolis, MN |
| 1975 | Michael E. Weaver United Dispatch, Inc. West Virginia | Indianapolis, IN |
| 1976 | Dean Benham Crouch Freight Systems, Inc. Kansas | Fort Worth, TX |
| 1977 | Carl A. Schneider Kroger Company Ohio | Kansas City, MO |
| 1978 | Augustin Guajardo, Jr. H.E. Butt Grocery Company Texas | St. Louis, MO |
| 1979 | Robert L Zesiger IML Freight Bountiful, UT | Phoenix, AZ |
| 1980 | Arthur W. Gruenbacher Consolidated Freightways Kansas | Kansas City, MO |
| 1981 | Charles Walker Overnight Transportation North Carolina | Indianapolis, IN |
| 1982 | Richard A. Gillespie Century Motor Freight, Inc. Blaine, MN | Kansas City, MO |
| 1983 | Clarence Hasbrook Super Value Stores, Inc. Hopkins, MN | Fort Worth, TX |
| 1984 | Arthur W. Gruenbacher Consolidated Freightways Kansas | Indianapolis, IN |
| 1985 | Charles L. Reynolds Transus, Inc. Oxford, GA | St. Louis, MO |
| 1986 | Charles Brown Franchise Services, Inc. Kansas | Kansas City, MO |
| 1987 | Ryland B. Hogan B.I. Transportation, Inc. Madison Heights, VA | Fort Worth, TX |
| 1988 | J. David Porter Conway-Central Express Inc., Ohio | St. Louis, MO |
| 1989 | Michael W. Neel H.E.B. Grocery Co. San Antonio, TX | Memphis, TN |
| 1990 | Dale Cox ABF Freight Ssystems California | Dallas, TX |
| 1991 | Michael J. Ripp TNT Red Star Express New Jersey | Minneapolis, MN |
| 1992 | Donald Sobba CF Motor Freight Kansas | Nashville, TN |
| 1993 | Gary W. Helgason CF Motor Freight Washington | Denver, CO |
| 1994 | John J. Hazlett ABF Freight System, Inc. Pennsylvania | Tampa, FL |
| 1995 | Johnny T. Ligon Southeastern Freight Lines South Carolina | New Orleans, LA |
| 1996 | Thomas B. Melton Giant Food District of Columbia | Columbus, OH |
| 1997 | Stephen Plonski J.P. Food Service Minnesota | Minneapolis, MN |
| 1998 | Gary L. Ott Roadway Express, Inc. Montana | Long Beach, CA |
| 1999 | Bruce M. Early Con-Way Central Express Inc Ohio | Tampa, FL |
| 2000 | John J. Hazlett ABF Freight System, Inc. Pennsylvania | New Orleans, LA |
| 2001 | Gerald W. Cudmore Yellow Freight System, Inc. South Dakota | Minneapolis, MN |
| 2002 | Richard Seigle Roadway Express, Inc. Illinois | Milwaukee, WI |
| 2003 | Gregory A. Nauertz Roadway Express, Inc. Arizona | Columbus, OH |
| 2004 | Randy S. Anton FedEx Freight North Dakota | Salt Lake City, UT |
| 2005 | Brent Darnold West Virginia | Tampa, FL |
| 2006 | Daniel Shamrell FedEx Freight Oregon | New Orleans, LA |
| 2007 | John J. Hazlett ABF Freight System, Inc. Pennsylvania | Minneapolis, MN |
| 2008 | Victor K. Wheeler Roadway Utah | Houston, TX |
| 2009 | Donald R. Logan FedEx Freight Kansas | Pittsburgh, PA |
| 2010 | Heladio "Lalo" Fernandez FedEx Freight Oregon | Columbus, OH |
| 2011 | John J. Hazlett ABF Freight System, Inc. Pennsylvania | Orlando, FL |
| 2012 | Roland G. Bolduc FedEx Express Massachusetts | Minneapolis, MN |
| 2013 | Roland G. Bolduc FedEx Express Massachusetts | Salt Lake City, UT |
| 2014 | Basher Pierce FedEx Freight North Carolina | Pittsburgh, PA |
| 2015 | Donald R. Logan FedEx Freight Kansas | St. Louis, MO |
| 2016 | Charles Mike WhiteWalmart Transportation, LLC Indiana | Indianapolis, IN |
| 2017 | Glen Kirk Old Dominion Freight Line Indiana | Orlando, FL |
| 2018 | Eric Courville FedEx Freight Louisiana | Columbus, OH |
| 2019 | Brian Walker UPS Freight North Carolina | Pittsburgh, PA |
| 2022 | Wilbert Vano XPO Logistics, Inc. New Jersey | Indianapolis, IN |
| 2023 | Barry Kraemer XPO Logistics, Inc. Wisconsin | Columbus, OH |
| 2024 | David Mogler FedEx Freight Colorado | Indianapolis, IN |
| 2025 | Daniel Shamrell FedEx Freight Oregon | Minneapolis, MN |
