Gray began his racing career running on the local dirt tracks around Rome, Georgia.  He quickly found he had a natural talent for driving on dirt.  He won many races in Georgia, Tennessee, and Alabama.  His early career on dirt lasted from around 1955-1964.  He continued to race and win on the dirt tracks after that, but he quickly learned that racing was what he wanted to do full time.  During these early years he was the owner of a junkyard in Rome called Grays Auto Parts.

In 1964 he ran his first NASCAR Grand National race in Nashville, TN starting 27th and finishing 20th.  The next year he competed in 38 of 55 races on the Grand National circuit with an average start of 19.6 and average finish of 17.4.  In 1966 he started 45 of 49 races with his best year in the point standings with a 4th place result coming from 4 top five and 18 top ten finishes.

On August 20th, 1977, Henley was involved in a single car practice crash caused by a parts failure.  The car made impact at the end of the pit wall shearing the left side of the car away and leaving him exposed.  He suffered major injuries in both legs.  After spending two and a half month in a hospital in Jackson, Michigan he was released to go home just before the final race of the season in Atlanta.  While Henley was recovering in the hospital his son Steve along with the help of many friends, especially John Ray of Eastaboga, AL loaned his racecar to finish out the year.  A young driver from the Charlotte, NC area made one of his early starts in this car, his name was Dale Earnhardt.

After returning home he began to put things together to continue racing the Grand National circuit.  He purchased another car and began preparing for the 1978 season.  Gray Racing continued racing each week until around 1981 when they began to run fewer races.  They competed in their final Winston C up race in 1993 at Michigan International Speedway with Clay Young, another Georgia driver.  The team continued running ARCA races with drivers that were looking to gain experience on big tracks but were not able to run the Cup series because of financial limitations.