Harry "Pee Wee" Oliver was a self-taught hockey player, perfecting his craft as a youngster on the frozen river near his home. "When I was a kid, there was no organized hockey," he explained. "We just went out and played, sometimes on an outdoor rink, but mostly on the river."
He played his junior and senior hockey with the Selkirk Fishermen before moving to Calgary to play with the Canadians of the Big-4 and the Tigers of the WCHL from 1920-21 to 1925-26. Although he was one of the lightest players in the league he had speed and grace of a thoroughbred, and was named to the WCHL First All-Star Team in 1924 and 1925. Harry Scott, Sports Editor of the Calgary Albertan, called him "smooth as silk," and he possessed great stick handling abilities and an accurate shot.
Oliver's behaviour was always exemplary, both on and off the ice. In his entire career, Oliver never spent more than 24 minutes in the penalty box during a season.
Harry was sold to the Boston Bruins on September 4, 1926 and played a total of eight seasons in Boston, winning the Stanley Cup in 1928-29. He was traded to the New York Americans on November 2, 1934, and stayed with the Amerks until he retired at the end of the 1936-37 season.
Harry Oliver was inducted into the Hockey Hall of Fame in 1967.