The trade provided immediate dividends for the Flames, as Kiprusoff recorded 22 saves in a 2–1 victory over the Montreal Canadiens in his first game with Calgary on November 20. He won 12 of 17 starts between November 20 and December 29, giving up one goal or fewer 11 times in that stretch. He was named the defensive player of the month for December by the league, but suffered a sprained medial collateral ligament in his knee at the end of the month that forced him out of the lineup for four weeks.
Kiprusoff's play remained strong upon his return as he was counted on to lead the Flames to the playoffs for the first time in eight years. A 1–0 victory over the Phoenix Coyotes clinched a berth in the 2004 Stanley Cup Playoffs for the Flames, an achievement which earned Kiprusoff a standing ovation from the Calgary fans. He finished the regular season with a modern NHL record low GAA of 1.69. His stellar play continued into the playoffs as he won 15 games, five of them by shutout, leading the Flames to within one victory of a Stanley Cup championship. He was named a finalist for the Vezina Trophy, awarded to the best goaltender in the league, and was given a one-year, $2.95 million contract for 2004–05 by an arbitrator, an increase in salary of nearly four times his previous contract.
As the 2004–05 lockout led to the cancellation of the season, Kiprusoff chose to play in Sweden. He played 41 games for Timrå IK, recording five shutouts and a 2.14 GAA. He remained a top goaltender for Calgary when NHL play resumed in 2005–06, breaking Mike Vernon's franchise record when he recorded his 40th win of the season, against the Minnesota Wild on April 8, 2006. He was not only touted as the top goaltender in the league, but also argued to be a candidate for the Hart Memorial Trophy as the most valuable player in the NHL. Finishing the season with a 42–20–11 record and a team record 10 shutouts, he was named a first team all-star and awarded the Vezina Trophy, as well as the William M. Jennings Trophy for being the goaltender on the team that gave up the fewest goals in during the season. He was also named a finalist for the Hart, though the award was won by Joe Thornton.
Kiprusoff struggled to begin the 2006–07 season, winning just four of his first 12 decisions, and giving up nearly three goals per game. He rebounded to finish the season with 40 wins, won his 100th career game, and played in his first All-Star Game. He recorded his 21st shutout in a Flames uniform in a 1–0 win over the Wild on March 27, 2007, to break Dan Bouchard's franchise record. Kiprusoff was outstanding in the 2007 Stanley Cup Playoffs, keeping the overmatched Flames close to the top seeded Detroit Red Wings despite the Flames giving up nearly 50 shots per game in their first two contests. He led them to consecutive wins in games three and four to even the series and gave the Flames hope they could win the series, but the Flames were unable to parlay his performance into a series win, losing the best-of-seven series 4–2. In game five, he was pulled after giving up five goals, but was forced to come back in only 18 seconds later when his backup, Jamie McLennan, was thrown out of the game for deliberately slashing the Red Wings' Johan Franzen. He earned his third consecutive nomination for the Vezina trophy, ultimately won by Martin Brodeur.
Nicknamed "Captain Hook" for the way he handled goaltenders, the Flames decision to hire Mike Keenan as head coach in 2007–08 created speculation that Kiprusoff might choose to leave Calgary when his contract expired at the end of the season. Nonetheless, he agreed to a six-year extension worth $35 million that would keep him in Calgary until the end of the 2013–14 season. He struggled at times, as his goals against average and save percentage fell outside of the top 30 goaltenders in the league by mid-November. His play improved throughout the season, and he finished the season third in the league with 39 wins.
Hoping to rebound in 2008–09, Kiprusoff arrived for the start of the season in better shape, but continued to struggle as he was questioned on whether his heavy workload the previous three seasons – he played 76, 74 and 74 games of a possible 82 – were taking a toll on him. He won his 200th career game on March 18, 2009, in a 2–1 victory over the Dallas Stars, but questions about whether he was playing too many games continued throughout the season. Although he led the league with 45 wins, his statistical averages had deteriorated for the fourth consecutive season as he admitted he struggled.
New head coach Brent Sutter promised that Kiprusoff would face a lighter schedule in 2009–10, he played 76 games in 2008–09, while Kiprusoff hired a personal trainer and set aside his previously indifferent attitude towards off-season training. His efforts appeared to pay dividends early in the season, as he lost only three of his first 17 decisions, leading his teammates to compare his early performance to his first years in Calgary. He finished in the top ten in the league in wins, save percentage and goals against average and while considered a potential candidate for the Vezina Trophy, he was not named a finalist in part due to the fact the Flames failed to qualify for the playoffs.
Kiprusoff, and the entire Flames team, struggled early in the 2010–11 season, and during a period of struggle late in January, he became a target of the fans' jeering. He admitted that he had struggled and was trying to focus on returning his play to where he felt it should be. Kiprusoff's fortunes improved in February, as he won his 250th game as a member of the Flames in a 9–1 victory over the Colorado Avalanche on February 14. Six nights later he became the first goaltender in NHL history to record a shutout in an outdoor game with a 4–0 victory over the Montreal Canadiens at the 2011 Heritage Classic. In a March 4 game against the Columbus Blue Jackets, he became the first goaltender in 25 years to stop two penalty shots in one game to preserve a 4–3 victory.
On February 8, 2012, Kiprusoff became the 27th goalie to record his 300th career win. He reached the mark with a 4–3 victory over the San Jose Sharks.
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