1997/98: For the second season in a row the Maple Leafs would struggle all season finishing in last place with a 30-43-9 record. Following the season as part of a major front office shake up the Leafs GM Pat Quinn would name himself head coach as former Montreal Canadiens Goalie Ken Dryden takes over as team president.
1998/99: With expansion the Maple Leafs are shifted to the Eastern Conference and into the Northeast Division with the rival Montreal Canadiens as part of a major realignment. However, the biggest move for the Leafs was the signing of Free Agent Goalie Curtis Joseph. I his first season with Leafs CuJo provide strong net minding as the Leafs made the playoffs with a solid 45-30-7 record. The year also sees the end of an era as the historic Maple Leaf Gardens closes in February as the Leafs open a brand new stadium complete with luxury suites downtown known as the Air Canada Centre. In the playoffs CuJo would be an immovable force as the Leafs knocked off the Philadelphia Flyers in 6 games. The Leafs would continue to stay hot as they beat Jaromir Jagar and the Pittsburgh Penguins in 6 games. However, in the Eastern Conference Finals the Leafs would run into a hot goalie themselves as Dominick Hasek and the Buffalo Sabres knocked beat the Leafs in 5 games.
1999/00: The Maple Leafs begin a new century in style as they crack the 100-point barrier for the first time in franchise history, while winning their first Division Title in 37 years with a 45-30-7 record. In the first round the Maple Leafs would win a battle of Ontario by beating the Ottawa Senators in 6 games. However, the Leafs would find themselves frustrated as they could not get past the New Jersey Devils neutral zone trap falling in 6 games.
2000/01: The Maple Leafs make the playoffs again finishing 3rd place in a competitive Northeast Division with a 37-29-11-5 record. In the playoffs the leafs would hit an extra gear, as goalie Curtis Joseph would shut down the 1st Place Ottawa Senators in a 4 game sweep. The Leafs continued to stay hoot as they battled the New Jersey Devils in the 2nd Round. However, the Leafs despite badly outplaying the Devils only held a 3-2 series lead, which allowed the Devils to breakout of their slump and beat the Leafs in 7 games. Making matters worse Leafs star enforcer Tie Domi is suspended for a cheap shot on Scott Niedermayer, a suspension that would carryover to the next season.
2001/02: The Maple Leafs hit the century mark again while finishing in 2nd place with a solid 43-25-10-4 record. However, the Maple Leafs would barely survive a 1st Round 7-game war against the New York Islanders in which several star players on each team including Leafs captain Mats Sundin were lost to injury. With a banged up team the Maple Leafs would have to gut things out again beating the Ottawa Senators in 7 games by rallying to win the final 2 games of the series after being dominated most of the series. However, even with return of Mats Sundin the Leafs would run out of gas falling to the Carolina Hurricanes in the Eastern Conferences finals in 6 games. Following the season the Leafs would fail in attempts to resign star goalie Curtis Joseph who bolted for the Detroit Red wings.
2002/03: The Maple Leafs would stumble out of the gate winning just 2 of their first 9 games, as the team adjusted to new goalie Eddie Belfour. However the Leafs began to find their way in mid October and quickly rode up the standings in the Northeast Division. However, their struggles against the Ottawa Senators would prevent them from getting over the top as the Maple Leafs won just 1 of 5 fight filled games with their rivals. Hoping to improve the team at the deadline the Maple Leafs made several big trades acquiring Owen Nolan from the San Jose Sharks, and reacquiring Leafs legend Doug Gilmour from the Montreal Canadiens. However the dreams of a great comeback from Gilmour were squashed early as he suffered a season ending knee injury, which ended his season and hi career as Gilmour announced his retirement after the season. The Leafs would go on to have another solid season finishing 2nd with a record of 44-28-7-3. In the playoffs the Leafs were matched up against the Philadelphia Flyers. After splitting the first 2 games in Philadelphia the Leafs took a series lead with a dramatic 4-3 win in double overtime on a goal by Tomas Kaberle. However, the Flyers would bounce back to take Game 4 in triple overtime. After losing Game 5 in Philly the Leafs staved off elimination with a 2-1 win in double OT on a goal by Travis Green. However, with Game 7 in Philadelphia the Leafs simply ran out of gas losing 6-1.
2003/04: The Maple Leafs continued to be one of the best teams in the Eastern Conference as they were in a 3-way dog fight with the Boston Bruins and Ottawa Senators for first place in the Northeast Division led once again by Mats Sundin who had a 75-point season. Hoping to put themselves over the top the Leafs acquired future Hall of Famers Brian Leetch from the New York Rangers and Ron Francis from the Carolina Hurricanes, both of whom were proven playoff tested winners. In just 15 games with the Leafs Leetch would notch 15 points as Francis had 10 in 12 games. However the Maple Leafs would fall 1 point short of a Division Title with a franchise record 103 points and a 45-24-10-3 record. In the playoffs the Leafs would draw the Ottawa Senators. After dropping Game 1 by a score of 4-2 the Leafs rebounded to win each of the next 2 games 2-0 as Eddie Belfour stopped a total of 68 shots. After a 4-1 loss in Game 4, the Leafs turned to Belfour again who stopped 21 shots in another 2-0 shutout win. Belfour looked to be heading for another shutout in Game 6, but the Senators rallied to win 2-1 in overtime to a force a 7th game. In Game 7 at the Air Canada Centre the Leafs would jump out to a 3-0 lead and never look back as they advanced to the second round with a 4-1 win. In the 2nd Round the Leafs would get off to a slow start as they dropped the first two games to the Philadelphia Flyers on the road. With the series shifting to Toronto the Leafs would come roaring back winning the next two to even the series. However in Game 5 their Philadelphia Horror continued as they were blow out 7-2. Needing a win at home to even the series the Leafs rallied with a pair of goals to force overtime in the 3rd Period. However, Jeremy Roenick would end the Leafs season with a goal at 7:39 of overtime to give the Flyers a 3-2 win.
2004/05: Season Cancelled Due to Lock Out
2005/06: Coming out of the lost season, the Maple Leafs, who were one of the oldest teams before the Lock Out, were even older and not any better, as the new Salary Cap tied their hands from being able to really make any key improvements. One player that was added was Eric Lindros who, once was touted to be the next big superstar, but with several injuries had become average at best. The Leafs started the season on the wrong foot as they were beaten by the Ottawa Senators 3-2 in the first shoot out in NHL history. After a mediocre October the Leafs played well through most of November and December, as they entered the New Year with a record of 22-14-3. However, in January the Maple Leafs would unravel enduring an 8-game losing streak as Goalie Ed Belfour struggled badly. Heading into the Olympic Break the Leafs continued their poor play as they slipped down the Eastern Conference Standings and found themselves in danger of missing the playoffs. During the Olympics in Torinio Maple Leafs Coach Pat Quinn already taking heat for the Leafs struggles led an unimpressive Canadian team that would not even play for a medal. When the season resumed the Leafs continued to fall as Lindros spent much of the second half on the injured list, as the Ed Belfour who became the second winningest goalie of all-time during the season was eventually benched with a 3.29 GAA and a .892 save percentage. Back up Mikael Tellqvist would not fair much better then Belfour as the Leafs held a 32-32-6 record on March 25th needing to almost run the table in April to have a shot at the playoffs. After Belfour and Tellqvist each struggled the Leafs called up Jean-Sebastien Aubin hoping that he could give them the goaltending they needed to finish the season strong. Aubin did better than anyone could have imagined posting a 9-2 record with both losses coming after regulation as the Leafs posted a strong 9-1-2 record over their last 12 games to finish with a record of 41-33-8, but it was not enough as they missed the playoff by just two points. It would also not be enough to save Pat Quinn's job as he was fired as both Coach Pat Quinn was fired and replaced by Paul Maurice. During the off-season the Leafs also went after goaltending help acquiring Andrew Raycroft form the Boston Bruins.
2006/07: Coming off their disappointing season the Maple Leafs retooled adding players like Pavel Kubina, Michael Peca, and Hal Gill to go along with new Goalie Andrew Rayfcroft. However, for most of the first three months the Maple Leafs played mediocre hockey, as they headed into the New Year with a 17-17-6 record. In January the Leafs started playing better despite losing Peca for the season with a knee injury. The Leafs would stay in playoff contention until the very end of the season as they held destiny in their own hands in the final week playing the New York Islanders and Montreal Canadiens in the final two games. However, a 5-2 loss to the Islanders put the Leafs on the brink as they needed a win over the Habs and an Islanders loss to get in. Led by three assists from Mats Sundin the Leafs would do their part beating the Canadiens 6-5 to knock their long time rivals out of contention. However, the Islanders would win their final game of the season, and edge the Leafs who finished 40-31-11 out of the playoffs by one point.
2007/08: The Maple Leafs struggles continued, as they got off to a poor start losing both ends to a season opening home-and-home to the Ottawa Senators, on the way to posting a mediocre 5-5-3 record in October. Things would get even worse in November as the Leafs dug a deep hole in the Northeast Division, by winning just 4-of-13 games. The Leafs would have a small hot streak in December as they won five of six, but they would win one of their next six games, as they entered the New Year, with fans calling for the firing of General Manager John Ferguson Jr. As the losing continued in January, fans would get their wish on January 22nd, when Ferguson was replaced by Cliff Fletcher on an interim basis. The Maple Leafs would never be a factor in the playoff chase as they finished in last place with a record of 36-35-11. As the season wound down it became apparent that Captain Mats Sundin, days as a Maple Leaf were numbered, as the team began to focus on rebuilding, and chose not to resign him at the end of the season. Also leaving the Leafs would be Coach Paul Maurice, who would be replaced by Ron Wilson.
2006/07: Coming off their disappointing season the Maple Leafs retooled adding players like Pavel Kubina, Michael Peca, and Hal Gill to go along with new Goalie Andrew Rayfcroft. However, for most of the first three months the Maple Leafs played mediocre hockey, as they headed into the New Year with a 17-17-6 record. In January the Leafs started playing better despite losing Peca for the season with a knee injury. The Leafs would stay in playoff contention until the very end of the season as they held destiny in their own hands in the final week playing the New York Islanders and Montreal Canadiens in the final two games. However, a 5-2 loss to the Islanders put the Leafs on the brink as they needed a win over the Habs and an Islanders loss to get in. Led by three assists from Mats Sundin the Leafs would do their part beating the Canadiens 6-5 to knock their long time rivals out of contention. However, the Islanders would win their final game of the season, and edge the Leafs who finished 40-31-11 out of the playoffs by one point.
2007/08: The Maple Leafs struggles continued, as they got off to a poor start losing both ends to a season opening home-and-home to the Ottawa Senators, on the way to posting a mediocre 5-5-3 record in October. Things would get even worse in November as the Leafs dug a deep hole in the Northeast Division, by winning just 4-of-13 games. The Leafs would have a small hot streak in December as they won five of six, but they would win one of their next six games, as they entered the New Year, with fans calling for the firing of General Manager John Ferguson Jr. As the losing continued in January, fans would get their wish on January 22nd, when Ferguson was replaced by Cliff Fletcher on an interim basis. The Maple Leafs would never be a factor in the playoff chase as they finished in last place with a record of 36-35-11. As the season wound down it became apparent that Captain Mats Sundin, days as a Maple Leaf were numbered, as the team began to focus on rebuilding, and chose not to resign him at the end of the season. Also leaving the Leafs would be Coach Paul Maurice, who would be replaced by Ron Wilson.