Montreal and St. Louis Conroy was selected in the sixth round, 123rd overall, at the
1990 NHL entry draft by the
Montreal Canadiens. He spent the majority of the
1994–95 season in the
American Hockey League (AHL) with the
Fredericton Canadiens, scoring 26 goals and 44 points in 55 games. he scored his first career
hat-trick on February 26, 1999, against the
Calgary Flames and finished sixth in Selke Trophy voting that season. He finished the season with just 27 points. 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, The Flames named him a co-captain along with
Bob Boughner late in the
2001–02 season, and he was the only captain in
2002–03. 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. 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. He later admitted that he did not truly wish to leave the Flames, but facing financial uncertainty with the
2004–05 NHL lockout looming, Conroy chose to accept the guaranteed contract. The lockout wiped out the first year of the deal, but he returned in
2005–06 to reach the 20-goal mark for the third time and 60 points for the second time in his career. An emotional Conroy, who said he was happy to return to Calgary, scored two goals the following night in his second debut with the Flames to defeat his former Kings teammates, 4–1. Conroy finished the season by scoring 21 points in 28 games for Calgary, then scored 34 points in
2007–08. He scored his 500th career point on January 3, 2009, when he assisted on
Todd Bertuzzi's game-winning goal in a 3–2 win against the
Nashville Predators, and finished the year with 48 points. The
2009–10 season proved a difficult one for Conroy, as he scored only three goals and 12 assists during a season shortened by wrist and knee injures along with a broken foot. He returned for another season as the Flames re-signed him to a one-year, two-way contract for the League minimum of $500,000. At the age of 39 years, Conroy
played his 1,000th NHL game, against the
Colorado Avalanche, on October 28, 2010. Only
Grant Ledyard was older (age 40) when he reached that milestone. One week later, on February 4, 2011, Conroy formally announced his retirement. ==Post-playing career==