sixth in Selke Trophy voting that season. He faced a difficult season in 1999–2000, however, as Joel Quenneville adopted a new strategy that abandoned the concept of a checking line. Conroy struggled at both ends of the ice, and frequently found his ice time limited as a result. He finished the season with just 27 points. Looking to improve their team for a playoff run in 2000–01, the Blues dealt Conroy, along with a draft pick, to the Calgary Flames for Cory Stillman. The trade was initially unpopular in Calgary, as the Flames had given up their leading scorer for Conroy, who noted that that was when he "learned not to read the papers or watch TV." Calgary and Los Angeles Opinion of the deal shifted considerably the following season as Conroy established himself as the Flames' first line center alongside Jarome Iginla. The pair developed good chemistry and became strong friends. Conroy scored career highs with 28 goals and 75 points, while Iginla reached the 50-goal plateau for the first time and led the NHL in scoring. Iginla credited Conroy for making his breakout season possible. Additionally, Conroy was named a finalist for the Selke Trophy for a second time. The Flames named him a co-captain along with Bob Boughner late in the 2001–02 season, and he held the role full-time in 2002–03. 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