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.
Cliff drove for Mike Boyle. 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 race. He was back next year 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 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.
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.