| Year | Winner | Location |
|---|---|---|
| 1940 |
Clyde Shepherd Asbury Transportation Co. Los Angeles, CA |
Chicago, IL |
| 1941 |
Clarence Maas McCracken Bros. Motor Freight Eugene, OR |
New York, NY |
| 1947 |
Chester W. Smith Reliable Transportation Co. Los Angeles, CA |
Los Angeles, CA |
| 1948 |
Chester W. Smith Reliable Transportation Co. Los Angeles, CA |
Washington, D.C. |
| 1949 |
John H. Castner Pierce Freight Lines Portland, OR |
Boston, MA |
| 1950 |
John H. Castner Pierce Freight Lines Portland, OR |
New York, NY |
| 1951 |
John H. Castner Pierce Freight Lines Portland, OR |
Chicago, IL |
| 1952 |
Harry M. Naylor Signal Trucking Service Los Angeles, CA |
New York, NY |