Cory Stillman's first year in the OHL was 1990-91 with the Windsor Spitfires where he collected 101 points in only 64 games. The next season saw Stillman selected by the Calgary Flames 6th overall in the 1992 NHL Entry Draft. His final year as a junior saw Stillman and his new team the Peterborough Petes go all the way to the Memorial Cup finals.
In Stillman's first season in the AHL with the Saint John Flames he led all rookies in scoring and made his NHL debut the next season while spending the majority of the year in Saint John. Stillman saw his first Stanley Cup playoff action in 1996 and was in Calgary for the better part of seven seasons before being dealt to the St. Louis Blues who were getting geared up for a Cup run in 2001. The Blues went all the way to the Conference Finals before falling to the eventual Stanley Cup winning Colorado Avalanche.
In his first full season with the Blues in 2001-02 Stillman scored 23 goals and finished with 45 points before establishing a career high 67 points the following year. After parts of three seasons with St. Louis, Stillman signed with the Tampa Bay Lightning in the summer of 2003 and went on to establish a career high in points with 80 (25-55-80) during the 2003-04 season and was instrumental in leading the Bolts to their first Stanley Cup title.
Following the lockout year of 2004-05, Stillman signed a three-year contract with the Carolina Hurricanes in the summer. Coming off a career year in Tampa Bay, Stillman was named the alternate captain of the Carolina Hurricanes prior to the start of the regular season. He continued to produce offensively notching 76 points in his first season as a Hurricane. His leadership and determined play motivated a young Hurricanes squad to finished second in the Eastern Conference. Stillman once again entered the NHL playoffs with an upstart Southeastern Division team, and once again was awarded the Stanley Cup. Stillman recorded at least a point in 21 of the 25 Hurricane playoff games and became only the sixth player in NHL history to win the Stanley Cup in consecutive seasons with two different teams.
Stillman returned to the Hurricane line-up in 2006-07, and mid-way through his season suffered a shoulder injury which sidelined the Peterborough, Ontario native for 31 games. He managed to record 27 points in 43 games that season on an inconsistent Hurricane club that failed to reach the playoffs. The following season, Cory Stillman appeared in 55 games with the Hurricanes before the club traded him with Mike Commodore to the Ottawa Senators for Joe Corvo and Patrick Eaves.
Stillman's stint in Ottawa was short lived however, after appearing in 24 regular season games his Senators were swept from the playoffs in the first round. In the off-season, Stillman signed a 3 year deal worth $10.6-million with the Florida Panthers.
On February 24, 2011, Stillman's time in Florida would come to an end. He was traded back to the Carolina Hurricanes, the club he had helped win the Stanley Cup back in 2006.