1923 V128-1 Paulin's Candy #46 “Hal” Winkler

Winkler started his professional hockey career with the Edmonton Eskimos of the Western Canada Hockey League in 1922. He would also play with the Calgary Tigers. In 1926, he moved to the New York Rangers of the National Hockey League. He would also play with the Boston Bruins who acquired him from the Rangers in a cash transaction on January 17, 1927.

According to Winkler's obituary in the May 31, 1956 edition of the Montreal Gazette, he was given the unflattering nickname "Baldy" because he had lost his hair at an early age. Winkler wore a modified baseball cap in goal partly because rival fans often threw objects at his hairless pate.

Winkler recorded 15 shutouts in 44 games for the 1927–28 Boston Bruins. Despite the NHL's regular season almost doubling in length from what it was in 1927–28, Winkler's mark is a single-season team record that still stands. Winkler recorded two playoff shutouts for Boston during the 1927 Stanley Cup playoffs. Both games were scoreless ties.

During the 1957–58 season the Stanley Cup was redone. Winkler's name was added to the Stanley Cup as a member of the 1929 Bruins. He played the whole season in the minors, as teams carried only one goaltender the backup goaltender would play for the teams minor league affiliate, for Winkler this was the Minneapolis Millers the Boston Bruins minor league team in the AHA. By adding Winkler's name to the Stanley Cup in 1957/58 it righted the wrong by not including his name when the player names were first stamped on the Cup.

His death at age 62 (wrongly reported as age 64 in the Montreal Gazette), came after "a lengthy illness." Winkler passed away at the Winnipeg General Hospital.