1999 – 2000 Calgary Flames season The 1999 – 2000 Calgary Flames season was the 20th National Hockey League season in Calgary . It featured a very young line - up , as befitted the " Young Guns " slogan the team was using at the time . 29 year old Steve Dubinsky was the oldest forward on the team when the season started . The Flames were pitting their hopes for ending their playoff drought on the off - season acquisition of 37 year old goaltender Grant Fuhr . The season started with young sniper Jarome Iginla holding out , as he was unable to come to a contract agreement with General Manager Al Coates . Despite lacking a contract , Iginla attended training camp , however he missed the first two games of the season before a deal could be reached . The Flames youth led to an inconsistent team , often bouncing between long winning and losing streaks . It took the Flames 20 games to win their first game in regulation time , however the team would break an NHL record on January 21 , 2000 by winning their eighth overtime game as Valeri Bure . At the end of the season the Flames set an NHL record by winning ten games in overtime . The Flames also struggled with injuries all season , losing 479 man - games to injury , and using a total of 45 players over the course of 1999 – 00 . As a result , the Flames would finish last in the Northwest Division , missing the playoffs for the fourth straight year . Following the season , the Flames cleaned house , firing Coates , and announcing they would not be offering head coach Brian Sutter and assistant coach Rich Preston new contracts . On the bright side for the Flames , two players were selected to participate in the 2000 NHL All Star Game , as Phil Housley represented the North American team , while Valeri Bure represented the European team . Rookie defenceman Robyn Regehr became the youngest nominee for the Bill Masterton Memorial Trophy in NHL history after he survived a serious car accident over the summer of 1999 that left him with two broken legs . Regehr would play 57 games for the Flames , but would not win the award . Prior to the season , the Flames lost right winger Ed Ward to the Atlanta Thrashers in the 1999 NHL Expansion Draft . The Flames also dealt Andreas Karlsson to the Thrashers in exchange for promises not to select certain unprotected players . Playoffs . The Flames finished 12th in the Western Conference , ten points behind the 8th place San Jose Sharks . Calgary failed to qualify for the playoffs for the fourth straight season . Player stats . Skaters . " Note : GP = Games played ; G = Goals ; A = Assists ; Pts = Points ; PIM = Penalty minutes " Denotes player spent time with another team before joining Calgary . Stats reflect time with the Flames only . Goaltenders . " Note : GP = Games played ; TOI = Time on ice ( minutes ) ; W = Wins ; L = Losses ; T = Ties ; GA = Goals against ; SO = Shutouts ; GAA = Goals against average " Transactions . The Flames were involved in the following transactions during the 1999 – 2000 season . Draft picks . Calgary ' s picks at the 1999 NHL Entry Draft , held in Boston , Massachusetts . The Flames had the 9th overall pick , however they traded down two spots to get Marc Savard from the New York Rangers . With the 11th overall pick , the Flames drafted Oleg Saprykin . Farm teams . Saint John Flames . The Baby Flames finished the 1999 – 2000 season with a . 500 record at 32 – 32 – 11 – 5 , good enough for 2nd place in the Atlantic Division . They would be swept in the first round of the playoffs by the Lowell Lock Monsters three games to none , however . Daniel Tkaczuk and Benoit Gratton led the team in points with 66 each , while Rico Fata led in goals with 29 . Ten different goaltenders suited up for the Flames , led by Jean - Sebastien Giguere , who started 44 games . References .