At the Amateur Draft the Leafs pick goalie Alex Fichaud 16th overall who turns out to be a dud.
Prior to the 1994–95 season, franchise player and fan favorite Wendel Clark was sent to the Quebec Nordiques in a blockbuster trade. Clark, along with defenceman Sylvain Lefebvre and Toronto's second pick in the 1993 NHL Entry Draft, Landon Wilson, were traded to the Nordiques on June 28, 1994, in exchange for forward Mats Sundin, defenceman Garth Butcher and Quebec's first pick in the 1992 NHL Entry Draft, Todd Warriner. In Clark's absence, the gritty and dependable veteran forward Doug Gilmour was named team captain.
After finishing fourth in 1992–93 and third in 1993–94, the Maple Leafs fell to fifth place in the Western Conference in 1994–95 and, for the first time in three seasons, they allowed more goals than they scored. The Maple Leafs appeared to be affected considerably by the loss of Clark. It was a shortened season (48 games) due to a lockout. Top scorer was Mats Sundin with 47 points but the duo of Doug Gilmour and Dave Andreychuk produced far less offense than in previous seasons. Gilmour who had finished the previous two seasons with 127 and 111 points dropped to just 33 points. Age and lack of size were catching up to him which put an end to any Stanley Cup hopes for Maple Leaf fans once again.
Throughout the regular season, Toronto never won more than two games in a row, and finished just two games above .500. To toughen up their lineup, the Leafs signed Warren Rychel from the Los Angeles Kings midway through the regular season, and on April 7, 1995, they traded center Mike Eastwood and a third-round pick in the 1995 NHL Entry Draft to the Winnipeg Jets in exchange for right wing Tie Domi.
Although the Maple Leafs were the underdogs against the fourth-place Chicago Blackhawks in the opening round of the playoffs, they won the first two games of the series at the United Center and went home to Maple Leaf Gardens for game three with two-games-to-none series lead. However, the Blackhawks played determinedly and won games three and four in Toronto to regain home-ice advantage in the series. Chicago then won game five, 4–2, and looked to clinch the series in game six back in Toronto. The Maple Leafs played a spirited game, going up 4–1 in the third period. The Blackhawks fought back with three consecutive goals to tie the game. At 10:00 of the first overtime period, Randy Wood scored his second goal of the game to give the Maple Leafs a 5–4 win. The victory tied the series at three games apiece and forced game seven back in Chicago. In game seven, Joe Murphy scored twice and Ed Belfour made 22 saves as Chicago advanced to the second round for the first time in three years with a 5–2 win.