Stillman grew up in Peterborough, Ontario playing hockey for the Minor Petes (OMHA) program. He also played competitive baseball. In 1989–90, Stillman played for the Peterborough Roadrunners Jr.B. (MTJHL) hockey club before being a 2nd round choice (27th overall) of the Windsor Spitfires in the 1990 Ontario Hockey League Priority Selection.\n', '

Stillman started his professional career in 1992, when he was drafted sixth overall in the first round by the Calgary Flames. Stillman was tried on both wings, and was quoted saying he liked the left side better but he can play right wing easily if needed. During the 2000–2001 season, Stillman was traded to the St. Louis Blues where he played for three seasons. At the 2003 entry draft, he was traded to Tampa Bay where he helped the Lightning win the Stanley Cup in June 2004.\n', '

During the free agent signing period following the end of the 2004–2005 NHL lockout, Stillman agreed to a three-year contract with the Carolina Hurricanes August 2, 2005. There, his team also won the Stanley Cup. He became the first player since Claude Lemieux to win consecutive Cups with different teams and the eleventh overall to do so.\n', '

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