Freeland served as a diesel mechanic with the US Navy in the South Pacific during World War II and started racing soon after his return from active duty racing track roadsters in Southern California.
Migrating to the Midwest with many of his colleagues in the early 1950s, he divided his time for a brief period between driving AAA sprint cars and serving as a self-proclaimed "stooge" on the Bob Estes Championship car that was under the joint care of Jud Phillips and A. J. Watson. Whenever Watson and Phillips needed a driver, they all joked, Freeland was ready to jump in, the Estes "ride" becoming his for five of the next six years.
Freeland competed in the Indy 500 eight times between 1953 to 1960. He was heading for a second place finish in 1955 when transmission failure put him out justd 22 laps from the finish. He was back in 1956 and posted his best result at Indy finishing third. He also finished 7th in 1954 and 1958.
A steady and reliable driver in AAA and USAC National Championship events who was almost invariably around at the finish, the laconic Freeland scored 36 top-10 finishes between 1952-60. He won four poles, led 134 laps of competition and had 10 finishes of either second or third. He ranked third in the 1956 USAC championship points standings.
For several years in the late 1950s and early 1960s, Freeland was one of several drivers who made quite an impact as a member of the Champion Spark Plug Company's Highway Safety program, in which "500" drivers would visit the nation's high schools to give safe-driving tips to students.
He died in San Diego after a period of declining health.