Winter won many Northampton Institute swimming titles at the turn of the century, when he was also the honorary secretary and treasurer of the club. He was also a half-back and captain of the Institute’s water polo team. Renowned as a long-distance swimmer, Winter took part in the 1899 Long-Distance Amateur Championship on the River Thames, which was won by the defending champion, John Jarvis. Winter later went on to become the long-distance champion of southern England. He also swam for the Zephyr Club.