Conroy was the Flames second-leading scorer in 2002–03 with 59 points and again in 2003–04 when he scored 47 points despite missing 19 games with a knee injury. Shortly before the 2003-04 season began, Conroy gave up the captaincy after having decided it was time for Iginla to take over leadership of the team. He reached two milestones that season; he scored his 300th career point against the Vancouver Canucks on November 29, 2003 and played his 600th game against the Detroit Red Wings on March 16, 2004. The Flames qualified for the 2004 playoffs, their first trip to the post-season in eight seasons. Conroy was a key player for the team as they upset the top three seeds in the Western Conference, the Canucks, Red Wings and San Jose Sharks en route to a seventh game loss to the Tampa Bay Lightning in the Stanley Cup Final. He finished second on the team in playoff scoring with 17 points. Following the season, Conroy was named to play with Team USA at the 2004 World Cup of Hockey, but appeared in only two games for the team.