Charles Winslow played three events at the 1912 and 1920 Olympics, winning a medal in each. He was gold medalist in singles and doubles at the 1912 Olympics, and added a bronze medal in singles in 1920. Winslow was South African singles champion in 1914. He played Wimbledon in 1920, losing in the second round of singles and the third round of doubles. He played one tie in the 1920 Davis Cup, winning both his singles matches and losing the doubles. Winslow came from an athletic family, as his father, Lyndhurst Winslow, was a top-level cricketer for Sussex County Cricket Club. His son, Paul, played cricket for South Africa between 1949-55.