Born on a ranch in Cardston, Alberta, his mother had been a trick rider in a circus and his father rode in rodeos. As such, Woolf was taught to ride horses as a child and as a teenager he rode in horse races and competed in rodeo events in Alberta and Montana. He began racing thoroughbreds professionally in 1928 in Vancouver, British Columbia before going to Tijuana, Mexico and then to Arcadia, California where he would make his permanent home.
Using Santa Anita Park as his home base, George Woolf became one of the premier jockeys of his era known by fellow jockeys and fans as "The Iceman." He earned the nickname not just because of his renowned patience in waiting for the right time to have his horse make a move, but also because of his totally calm attitude even before major races when he would often take a nap while other jockeys nervously paced about.
While he was establishing himself as one of America's leading jockeys, he was diagnosed with what is now known as type 1 diabetes. Only a few years earlier, before the discovery of insulin, such a diagnosis would have been a death sentence. Because of his condition, and the nature of diabetes management in the 1930s and 1940s, Woolf had to regulate his weight so as never to be in a position where he would be forced into rapid dieting. His racing success allowed him to accept only a few mounts each week and for years that kept him in the best possible physical condition. Despite his limited number of races and the fact that he had a relatively short career, George Woolf won ninety-seven major stakes races around the United States including the Hollywood Gold Cup Stakes, the American Derby and the Belmont Futurity Stakes three years running. He made history in 1935 when he rode Azucar to victory in the first $100,000 horse race, the Santa Anita Handicap, defeating such greats as Equipoise and Twenty Grand. Woolf finished second twice at the Kentucky Derby and won the 1936 Preakness Stakes. He is also remembered for his tactical performance in the famous 1938 match race when he rode Seabiscuit to victory over the heavily favored U.S. Triple Crown champion War Admiral in the Pimlico Special.
During the running of the fourth race at Santa Anita Park on January 3, 1946, George Woolf fell from his horse as he rounded the clubhouse turn. Suffering from a concussion, he was taken to hospital where he died the following day. Both the jockeys in the race and the track stewards reported that they had not witnessed any incident that would have caused such a fall and it is generally believed his diabetic condition may have resulted in him suffering a dizzy spell or fainting.
The shocking death at the age 35 of one of the country's best and most respected jockeys, and a favourite of fans, led to the creation of the George Woolf Memorial Jockey Award. During his career (1928-1946) Woolf had 3,784 mounts, 721 wins (19.1%), 589 seconds and 468 thirds. Following its creation, George Woolf was an inaugural inductee into the National Museum of Racing and Hall of Fame in 1955  and Canada's Sports Hall of Fame in 1956.  He was part of the inaugural class inducted in the Canadian Horse Racing Hall of Fame in 1976. 
When asked which was the best racehorse he'd ever ridden, Woolf answered immediately, "Seabiscuit."
Marking the 100th anniversary of George Woolf's birth, a life-size equestrian statue is being created for placement in his home town of Cardston, Alberta. The bronze statue depicts Woolf riding Seabiscuit to victory in the 1938 match race against War Admiral. Woolf's birthday is May 31, and the unveiling of the statue is scheduled for July 17, 2010, on the grounds of the Remington Carriage Museum in Cardston.