He played junior hockey with the Toronto Native Sons from 1937 to 1940. Webster then played for the Baltimore Orioles in 1940-41 and the senior St. Catharines Saints in 1941-42 before joining the Canadian Army in World War II.
After the war Webster joined the Baltimore Clippers of the Eastern Hockey League and then moved up to the New Haven Ramblers of the American Hockey League. While with the Ramblers, Webster earned a callup to the New York Rangers in 1949-50 for 14 games, during which he was held scoreless but got 4 minutes in penalties.
He played the rest of his career in the minor pros and seniors, retiring in 1953.