Shouldice competed in the Nor-Am Cup in January 1999 . He made his debut in the World Cup on January 12, 2003 at Mont Tremblant , where he finished 30th. The best result in its inaugural season was a sixth place. On January 11, 2004, he achieved his first podium finish when he was also second on Mont Tremblant. In the following 2004/05 season, a second place was his best result. At the 2005 World Cup in Ruka , he came in ninth.
On December 16, 2005, Shouldice celebrated its first World Cup victory in Changchun . In the same winter a second and a third place followed. At the 2006 Winter Olympics , he was fifth. Due to an injury, Shouldice had to take a break for the entire 2006/07 season. There were two podium places in the 2007/08 World Cup season, as well as in the 2008/09 season. In Inawashiro , Japan , he won the bronze medal at the 2009 World Cup .
Shouldice finished the 2009/10 season with another podium, and at the 2010 Winter Olympics he jumped to tenth place. On January 29, 2011, he won the second World Cup in front of a home crowd in Calgary. At the 2011 World Cup , he achieved the greatest success of his career by winning the gold medal.