He started out in senior hockey with various teams in Winnipeg from 1913-19, most notably the Winnipeg Ypres. He then played for the senior Brandon Elks, Moose Jaw Maple Leafs, and Saskatoon Crescents from 1919-21. Winkler started his professional career with the Edmonton Eskimos of the Western Canada Hockey League in 1922. He also played with the Calgary Tigers in 1924-25 and 1925-26. In 1926 when the Western League collapsed, he moved to the New York Rangers of the National Hockey League. He also played with the Boston Bruins. He spent three seasons in the minor pros before retiring in 1931.