[1][2] Beginning in 1931 he crewed for Howard McMichael on the two-man Star class Grey Fox, and in 1934 he bought the boat and renamed it the Jay.
[1][3] He won over 47 regattas, and was a frequent competitor in the Star World Championships;[3] his best finishes were second in 1947 (crewing for Hilary Smart) and third in 1949 and 1951 (both with his own boat, Flame).
[6] The C. Stanley Ogilvy Masters Trophy, an antique sextant awarded to a sailor over the age of 50, was named in his honor and has been presented annually by the Etchells World Championships since 1999.
[1][2] During World War II, his bad eyesight preventing him from serving in the Navy; instead he became the commander of a rescue boat on the Pacific Front for the U.S.
[1][2][3][9] His thesis, supervised by Walter R. Baum, was entitled An Investigation of Some Properties of Asymptotic Lines on Surfaces of Negative Gaussian Curvature.