| Year | Winner | Location |
|---|---|---|
| 1958 | Hayter C. Brown The Mason & Dixon Lines, Inc. New Market, VA | Miami Beach, FL |
| 1959 | Paul P. Rogers O'Boyle Tank Lines Maryland | Louisville, KY |
| 1960 | Lewis D. Gooch Esso Standard Oil Company Richmond, VA | St. Paul, MN |
| 1961 | William F. Roesel Roesel Fuel Oil Service Winston Salem, NC | Detroit, MI |
| 1962 | Richard C. Wilke The Mason & Dixon Lines, Inc. New York City, NY | Dallas, TX |
| 1963 | Daniel T. Smith F.J. Egner & Son, Inc. West Richfield, OH | Miami Beach, FL |
| 1964 | Alfred V. Miller The Willett Company Chicago, IL | Louisville, KY |
| 1965 | Billy G. Kirby Hennis Freight Lines Winston Salem, NC | Kansas City, MO |
| 1966 | Richard C. Wilke The Mason & Dixon Lines, Inc. New York City, NY | Minneapolis, MN |
| 1967 | Arnold Alcorn Standard Oil Company Minnesota | Tulsa, OK |
| 1968 | John Jennings Overnite Transportation South Carolina | Cincinnati, OH |
| 1969 | Frank Hutton Mason & Dixon Lines, Inc. West Virginia | Denver, CO |
| 1970 | William L. Hannibal, Jr. Humble Oil & Refining Co. Maryland | Miami Beach, FL |
| 1971 | Richard D. Brafford Mason & Dixon Lines, Inc. | Houston, TX |
| 1972 | Eldon O. Tickle Mason & Dixon Lines, Inc. Virginia | Louisville, KY |
| 1973 | George W. Snyder Mason & Dixon Lines, Inc. Pennsylvania | Denver, CO |
| 1974 | James R. Garinger Continental Oil Co. Colorado | Minneapolis, MN |
| 1975 | Frank M. Hutton Mason & Dixon Lines West Virginia | Indianapolis, IN |
| 1976 | Robert A. Dotson Mason & Dixon Lines, Inc. North Carolina | Fort Worth, TX |
| 1977 | Harlan J. Diers Super Valu Stores, Inc. Minnesota | Kansas City, MO |
| 1978 | Robert W. Sherman Exxon Company, U.S.A. | St. Louis, MO |
| 1979 | Frnak M. Hutton Mason & Dixon Tank Lines Hurricane, WV | Phoenix, AZ |
| 1980 | Larry Ryder Pennzoil Charleston, WV | Kansas City, MO |
| 1981 | Ronald J. Bowman, Sr. Getty Refining & Marketing Pannsylvania | Indianapolis, IN |
| 1982 | Robert E. Friend Advanced United Expressways St. Anthony, MN | Kansas City, MO |
| 1983 | Wayne Foble Giant Food, Inc. Jessup, MD | Fort Worth, TX |
| 1984 | Ralph K. Lange Matlack, Inc. New Jersey | Indianapolis, IN |
| 1985 | James R. Hanson Milwaukee Motor Transportation Wood Dale, IL | St. Louis, MO |
| 1986 | William A. Engle Mobil Oil Corporation New Jersey | Kansas City, MO |
| 1987 | Reginald B. Hamm Petroleum Carriers, Inc. Sturbridge, MA | Fort Worth, TX |
| 1988 | Clifford E. Williams B.I. Transportation Georgia | St. Louis, MO |
| 1989 | Robert W. Sherman Exxon Company, U.S.A. Richmond, VA | Memphis, TN |
| 1990 | David E. Knight Publix Super Markets Florida | Dallas, TX |
| 1991 | Richard Gillespie Star Tribune Newspaper Minneapolis, MN | Minneapolis, MN |
| 1992 | Wiley Price Murray Envelope Corp. Mississippi | Nashville, TN |
| 1993 | Dcecil H. Wolfe DSI Transport, Inc. Virginia | Denver, CO |
| 1994 | Robert D. Steelman Exxon Company U.S.A. North Carolina | Tampa, FL |
| 1995 | Keith Mergner Roadway Express, Inc. New Jersey | New Orleans, LA |
| 1996 | Robert W. Taylor Robinson Terminal Warehouse District of Columbia | Columbus, OH |
| 1997 | Larry L. Ripley Matlack. Inc. New York | Minneapolis, MN |
| 1998 | Frederick H. Schenk DeMoulas/Market Basket Massachusetts | Long Beach, CA |
| 1999 | Earl B. Rosado Hawaii | Tampa, FL |
| 2000 | David E. Knight Publix Super Markets Florida | New Orleans, LA |
| 2001 | Norman Melanson Virginia | Minneapolis, MN |
| 2002 | Dale Knox Con-Way Central Express Pennsylvania | Milwaukee, WI |
| 2003 | Weldon L. Runnels Wal-Mart Transportation, LLC Colorado | Columbus, OH |
| 2004 | Ronald J. Bowman, Sr. New Jersey | Salt Lake City, UT |
| 2005 | Michael Lomastro Publix Supermarkets, Inc. Florida | Tampa, FL |
| 2006 | Dale Duncan Con-Way Freight California | New Orleans, LA |
| 2007 | Dale L. Duncan Con-Way Freight California | Minneapolis, MN |
| 2008 | John A. Smith, Jr. FedEx Ground Mississippi | Houston, TX |
| 2009 | Anthony J. Spero ABF Freight System, Inc. Connecticut | Pittsburgh, PA |
| 2010 | Carl T. Krites Con-Way Freight Ohio | Columbus, OH |
| 2011 | Leo R. Flack A. Duie Pyle, Inc. Pennsylvania | Orlando, FL |
| 2012 | Brent L. Quire Con-Way Freight Kentucky | Minneapolis, MN |
| 2013 | Ina L. Daly Con-Way Freight Arizona | Salt Lake City, UT |
| 2014 | Christopher Miller United Petroleum Transportation Oklahoma | Pittsburgh, PA |
| 2015 | Brian Singelais A. Duie Pyle Massachusetts | St. Louis, MO |
| 2016 | Jeffery Langenhahn XPO Logistics, Inc. Wisconsin | Indianapolis, IN |
| 2017 | Scott Woodrome FedEx Freight Ohio | Orlando, FL |
| 2018 | Scott Woodrome FedEx Freight Ohio | Columbus, OH |
| 2019 | Paul Brandon FedEx Freight Connecticut | Pittsburgh, PA |
| 2022 | Michael Flippin FedEx Freight Colorado | Indianapolis, IN |
| 2023 | James Wilson United Parcel Service Inc. Nevada | Columbus, OH |
| 2024 | Jackie Reed FedEx Freight Mississippi | Indianapolis, IN |
| 2025 | Jeff Langenhahn XPO Wisconsin | Minneapolis, MN |
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