1999 – 2000 Toronto Maple Leafs season The Toronto Maple Leafs finished in first place for the first time since the 1962 – 63 NHL season . It was also the Maple Leafs first 100 - point season . It was also Wendel Clark ' s last season in the NHL . Regular season . The Leafs had their second consecutive 45 - win season , and broke the 1992 - 93 franchise record for most points in a season . Mats Sundin averaged a point per game , scoring 32 goals and picking up 41 assists for 73 points in 73 games . Jonas Hoglund had a career year , finishing third on the team in points with 56 ( 29 goals , 27 assists ) . Curtis Joseph set a Leafs record for wins in a season by a goaltender with 36 . The Leafs put Steve Sullivan on waivers and on October 23 , 1999 he was picked up by the Chicago Blackhawks . In early 2000 , Wendel Clark returned to the Leafs for the third time and had a two goal game on February 1 in a 5 - 3 Leafs win at Tampa Bay . In March , the Leafs traded Mike Johnson to the Tampa Bay Lightning for Darcy Tucker . The Leafs got off to a red - hot start to the season , winning 10 of their first 14 games with 4 shutouts . The team suffered a setback on December 4 , 1999 in a home game against the Pittsburgh Penguins . Forward Yanic Perreault was coming around the Pittsburgh net with the puck when Penguins goaltender Tom Barrasso slashed Perreault with his goalie stick . Perreault suffered a broken arm and missed 23 games . Barrasso received a 4 - game suspension . Another setback occurred on March 11 at Ottawa when Marian Hossa was attempting to clear the puck out of the centre - ice zone . Hossa swung his stick in a golf - swing motion and caught Toronto defenseman Bryan Berard in his right eye . Berard had to leave the game due to the injury and Hossa was assessed with a double minor for high - sticking . It was the last NHL game Berard would play for nearly a year and a half . To make matters more complex , Sergei Berezin , a 37 - goal scorer in 1998 - 99 missed 21 games . He finished with a solid 26 goals . Despite losing these hindrances , the Leafs battled on , defeating 4 stellar teams between March 16 and April 1 ( Detroit on March 16 ; New Jersey on March 25 ; St . Louis on March 29 ; and Washington on April 1 ) . The Leafs finished 3rd in the Conference and 1st in the Northeast Division . Sundin led all skaters in overtime goals scored , with 4 . All - Star Game . The 50th National Hockey League All - Star Game was part of the 1999 – 2000 NHL season , and took place in Toronto ' s Air Canada Centre on February 6 , 2000 . The all - star week festivities saw the Canadian Hockey League Top Prospects Game played on February 2 , and an exhibition game between the Canadian and American women ' s national teams on February 3 . The Heroes of Hockey game and the Skills Competition were held on February 5 . It is to note that the opening face - off for the Heroes of Hockey game were Ted Lindsay and Fleming Mackell , two players who played in the 1st National Hockey League All - Star Game . The week also was a good sendoff for Wayne Gretzky , who had retired the previous season . His # 99 was raised to the rafters , despite him never playing for the hometown Toronto Maple Leafs , as a show of his number ' s league - wide retirement . Gretzky also made it clear that he would not partake in any oldtimer or Heroes of Hockey game unless it was held in Edmonton , a statement that was realized with the Heritage Classic three years later . Transactions . The Maple Leafs have been involved in the following transactions during the 1999 - 2000 season .