Wooldridge enlisted as a private in Co. C of the 9th VA Infantry on September 9, 1861, and is listed as a substitute for Edwin S. Wooldridge, who was his older brother. He was discharged on December 10, 1861 upon furnishing a substitute. He enlisted as a private in Parker's Virginia Battery of Huger's Artillery on August 24, 1863 and it is unclear when he reported for duty, although he was paroled at Appomattox Court House on April 9, 1865 and his older brother Edwin was commanding the unit at that time.
After the war, he moved to Manchester, VA (now part of Richmond) and was a coal merchant in 1870 and a farmer in 1880. Wooldridge died in July 1896 and is buried in Richmond's Hollywood Cemetery.
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