Stephens was highly rated as a young player and was selected first overall in the Ontario Hockey League entry draft, and attained national prominence for his role in the Esquire Swiss Watch company's advertising. He was selected in the second round of the 1999 NHL Entry Draft by the Washington Capitals, but did not sign with them and ultimately was re-drafted in 2001 by the Colorado Avalanche.
After a long OHL career with the Toronto St. Michael's Majors, Guelph Storm and London Knights, Stephens turned pro, but to date has only played 8 NHL games, all with Colorado. On January 23, 2004 Stephens was traded to the Ottawa Senators for Dennis Bonvie.[1] However Stephens never played for the Senators spending most of his time with the Binghamton Senators.
For the season 2006–07 he signed a contract with the DEG Metro Stars of the Deutsche Eishockey Liga. In 2008, Stephens then signed for rivals the Krefeld Pinguine instantly becoming an integral part of the team.[2]
After his third season with the Penguins, Stephens left as a free agent and signed a two-year contract to remain in Germany with Kölner Haie on April 12, 2011.[3]