As well as the Flames, he would go on to play for the St. Louis Blues, Tampa Bay Lightning, Carolina Hurricanes, Ottawa Senators, and Florida Panthers over his 15-year NHL career, scoring over 700 points over more than 1,000 games.

This game would turn out be a 5–4 home defeat against the Winnipeg Jets, and Stillman recorded his first NHL point on a 3rd-period assist on what was, at the time, the go-ahead goal before the Flames faltered late.

The Blues finished the regular season with 103 points and were the #4 seed in the Western Conference, and made it to the Western Conference Finals, avenging an upset in the first round against the San Jose Sharks in the previous season as well as sweeping the Pacific Division champion Dallas Stars in the second round before losing four games to one to the eventual Cup winners in the Colorado Avalanche.

A pending free agent at the end of the 2003–04 season, he was traded during the off-season to the Tampa Bay Lightning for a draft pick that eventually turned out to be long-time Blues stalwart, and later captain, David Backes.

The Lightning would win 25 of their final 36 regular season games, with Stillman scoring 11 goals and 46 points coinciding with this spurt.

During the 2004 NHL Entry Draft, the Lightning re-acquired Prospal and did not re-sign Stillman, who hit free agency on July 1, 2004.

During the free-agent signing period following the end of the 2004–05 NHL lockout, Stillman agreed to a three-year contract with the Carolina Hurricanes August 2, 2005.

He became the first player since Claude Lemieux to win consecutive Cups with different teams, being the eleventh overall and most recent to do so until Patrick Maroon accomplished the feat in 2020.

[2] Stillman waived his no-trade clause February 11, 2008, so that the Hurricanes could trade him along with Mike Commodore to the Ottawa Senators for Patrick Eaves and Joe Corvo.

On February 17, 2011, Stillman played his 1,000th NHL game against the Philadelphia Flyers at BankAtlantic Center in Sunrise, Florida.

The Florida Panthers traded Stillman back to the Carolina Hurricanes on February 24, 2011, in exchange for Ryan Carter and a fifth-round pick in the 2011 NHL Entry Draft.

The Stillmans have three children, Riley, Madison and Chase, who plays for the New Jersey Devils AHL affiliate team, the Utica Comets.