Wickenheiser was born in 1978 and grew up in Shaunavon, in the province of Saskatchewan. The oldest of three, she first learned to skate at the age of six when her parents created a backyard ice rink with the help of a garden hose and some two-by-fours. She played her first hockey games on it, and was soon devoted to the sport; her father once woke in the middle of night to find her out in the backyard taking shots. As a youngster, she joined a local team as its sole female participant, at a time when organized hockey for female players was almost nonexistent.
Often there was no available dressing room for her to use, and she was forced to don her gear in boiler rooms or other areas of the rink. Her mother battled to have her enrolled in a hockey school in Swift Current, Saskatchewan, and again, she tested her mettle as the only player of her gender there. When she was in middle school, the Wickenheiser family relocated to Calgary, Alberta, so that she could play on an all-girls' team in the city.
At fifteen, Wickenheiser made the Canadian women's national team, and joined players who were, in some cases, twenty years her senior; they nicknamed her "High-Chair Hayley" because of her youth. With Team Canada she went on to play in winning World Championship contests in both 1994 and 1997. She had also become an outstanding softball player, and made the Canadian junior women's team in 1995. Women's ice hockey became an Olympic medal sport for the first time at the 1998 Nagano Winter Olympics in Japan, and though Wickenheiser and her Canadian team were heavily favored, they suffered an upset to the United States and went home with the silver medal instead. Her on-ice performance impressed Bobby Clarke, the Philadelphia Flyers president who served as general manager of the men's Olympic hockey team, and he invited her to the Flyers prospects' camp that summer. Wickenheiser realized that her chances for a contract were slim, but she relished the chance to compete against other Olympic-caliber players. "I'm basically just seeing it as a chance to improve my game," she told Maclean's