Finished 3rd at Indy on his first attempt in 1926 in a rain shortened race. Returned to the brickyard three more times, putting his Miller on pole in 1929 but going out on the third lap after he tangled with Leon Duray. He has the distinction of posting the worst finish for any pole sitter in the history of the Indy 500.
Born in Chicago, Illinois, Cliff raced all over the US during one of the most dangerous times in motorsports.
He started racing at state fairs across the Midwest in around 1915. Racing a Duesenberg he won purses that sometimes amounted to more than $500. In 1921 and 1922, he worked with Ruth Law with her barnstorming Flying Circus which paired a race car and bi-plane. The highlight of the show was when a female daredevil would climb a ladder from the Cliff's race car to the plane while both were racing around the track.
Woodbury was a popular local hero at the motor sports tracks in Chicago and appeared often in The Chicago Tribune with his Fronty Ford. AAA named Cliff the Dirt Tack Champion of the Nation in 1924, 1925 and 1926.
In 1926, Woodbury joined Mike Boyle's Boyle Valve Racing Team and began his career on board tracks driving supercharged Millers. Boyle was a union leader from Chicago who had caught the racing bug. He started owning cars in 1926 when he entered an old Miller driven by Woodbury that finished third in that rain shortened Indy 500 that year.
He was back in 1927 with two new Millers for Woodbury and Ralph Hepburn. Woodbury was classified 19th have gone out on lap 108 with supercharger problems.
For 1928 Boyle bought two new Miller front wheel drive cars. Woodbury was the lead driver and Fred Comer was the second driver and mechanic. Comer was ninth while Woodbury who qualified second fastest, was 23rd after an engine failure. By comparison the two older Boyle Millers finished seventh and twelfth driven by Billy Arnold and Dave Evens.
Late in 1928, Comer crashed Woodbury’s car and in 1929 Woodbury drove Comer’s car. With it he took pole in qualifying for the Indy 500 with a speed of 120.599mph. Unfortunately Cliff tangled with Leon Duray competing for the lead early in the race and crashed in the fourth turn on lap four. He has the distinction of posting the worst finish for any pole sitter in the history of the Indy 500.
Woodbury retired after a severe wreck in Altoona, Pennsylvania in June 1929 which killed the 1929 Indy 500 winner, Ray Keech. Though the car was repaired and was used for one final time in a record run on the sands of Daytona in 1930 where Woodbury was timed by AAA at 180.90 MPH.
After retirement Woodbury established a successful auto repair business "Woodbury Bros" with his brother Elmer which was based in Chicago. He died in 1984 in Alton, Illinois.