The Flames re-signed Conroy to a new contract prior to the 2008–09 season and named him an alternate captain. 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.