Like other Canadian kids growing up in the early 1900s, Harold Darragh learned to play hockey on the frozen ponds during the harsh Canadian winters.
As a young man Darragh and friend Hib Milks moved to Pittsburgh to play with the Yellow Jackets, a minor-pro team. Harold Cotton and Lionel Conacher were teammates of Darragh. He was known as being one of the cleanest players in any game, rarely taking needless penalties.
After a couple of years leading the minors, Darragh moved up to the NHL's Pittsburgh Pirates, where he produced five productive seasons of what would be an eight-year NHL career.
In 1925-26, Darragh played in 35 games, scoring ten goals while assisting on seven others with only six minutes in penalties. He followed that up with a 42-game performance the next year, scoring 12 times while assisting on three others. His most effective offensive season came in 1929-30, at the age of 26, when he scored 15 goals and 17 assists for 32 points in 42 games.
In 1930-31 he divided his time between the Philadelphia Quakers and the Boston Bruins before playing a 48-game season with the Toronto Maple Leafs in 1931-32.
Never one to shy away from a confrontation, Darragh's aggressive, yet clean style often resulted in his receiving injuries, the most notable of which came during his stay with the Bruins, when shortly after arriving, he received a serious leg injury which tied him up for the better part of the season.
When the Bruins asked for waivers on Darragh, the Toronto Maple Leafs purchased his rights for $5,000. He joined the club the same year historic Maple Leaf Gardens opened its doors. Darragh scored five times and assisted on ten others that year and helped the team win the Stanley Cup, with the legendary Dick Irvin behind the bench. He returned to the Leafs for 19 games in 1932-33, scoring once and adding two assists. That would mark the end of his NHL playing days. His professional hockey career ended after the 1935-36 season, where he played for the Pittsburgh Shamrocks of the IHL.
The final statistics on Darragh's NHL career read 308 games played, 68 goals, 49 assists, 117 points and just 50 minutes in penalties.