Woolstencroft represented Canada at the 2002 Winter Paralympics in Salt Lake City, winning two gold medals and a bronze. She represented her country again at the 2006 Games in Turin, winning gold in the Giant Slalom and silver in the Super G. For her performance at the 2006 Games Woolstencroft was named Best Female at the Paralympic Sport Awards. She had contemplated retiring after the 2006 Games, but decided to stick around through the 2010 Games in Canada.