The son of an auctioneer, Henry Winkworth was educated at Harrow (1918-24) where he was a fine track athlete, notably a sprinter. After Harrow, he went up to Jesus, Cambridge, and in his first year got the seat as cox to the college rowing eight. Although he never won a Blue, he did take part in several Boat Race practice crews. He competed at Henley on two occasions, for Jesus College in 1924 and for London Rowing Club (LRC) in the 1929 Grand. He also had the misfortune of being cox to the 1936 LRC eight when they lost the Head of the River Race for this first time since its inception in 1927. Winkworth was also a fine golfer and won many local and Old Harrovian tournaments. He served in the Royal Navy in World War II. After leaving University, he became a land and estate agent.