In the period from 1929 to 1939 he won nine national championship titles in men's singles and five in pair skating with his sister Constance Wilson . He holds the record for the most victories in Canadian figure skating championships. 1932 was his most successful year on the international stage. He was runner-up behind Karl Schäfer and won the bronze medal at the Winter Olympics . In both tournaments he also started in the pair skating competition with his sister and reached sixth place at the World Championships and fifth place at the Winter Olympics. Wilson focused on the Olympic years and otherwise rarely took part in tournaments. In 1936 he came back after a four-year international break and again achieved fifth place at the World Figure Skating Championships and fourth place at the Winter Olympics .
Wilson was the first Canadian who could win a medal in men's singles at world championships and also at the Olympic Games. With this he established a long tradition in figure skating in Canada.
After his active sports career, he worked for several years as a coach at the Boston figure skating club. He died in 1964 at the age of 55.