At the Amateur Draft the Leafs pick Cereda 24th overall who never even plays a game in the NHL. 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. He would go on to score 208 goals and 544 points with Chicago and and Nashville over the next 10 season. 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 made their biggest trade of the season when they sent Mike Johnson to the Tampa Bay Lightning for Darcy Tucker. That trade was more or less neutralized by an earlier trade with Tampa Bay when the Leafs flipped Fredrik Modin for Cory Cross. Also that season the Leafs picked up Dmitri Khristich from Boston after a contract squabble with Bruins GM Harry Sinden. He was a given a substantial contract but was a total bust scoring only 30 points in 53 games wit the Leafs.
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 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.
The Leafs finished 3rd in the Conference and 1st in the Northeast Division. The Leafs finished in first place for the first time since the 1962–63 NHL season. Sundin led all skaters in overtime goals scored, with 4.
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 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.
In the playoffs the Maple Leafs overwhelmed a young Senators team and won their first round series 4-2. However, the New Jersey Devils were a tougher match and took the Leafs 4-2. The neutral zone trap carried the Devils to the Stanley Cup and the message wasn't lost on Pat Quinn who determined the Leafs needed to get bigger and tougher.
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