January 2, 1992 - The Day Dougie Arrived
Or as I call it, the day that Doug Risebrough lost his brain. The moment that Doug arrived in Toronto, it saved the Leafs' season. Many people call the trade the most lopsided trade in history. Doug Gilmour, Rick Wamsley, Rick Nattress, Jamie Macoun, Kent Manderville went to the Leafs. Going to the Flames, Greg Berube, Alexander Godynyuk, Gary Leeman, Michel Petit, and goaltender Jeff Reese. To this day, many people feel it cost Risebrough his tenure in Calgary as the GM.
Leafs vs. Isles 1978 Playoffs
Lanny Macdonald's goal in game seven vs. the Isles was awesome. The series itself was billed as David vs. Goliath. But it turned into a classic, each team taking momentum back and forth. What made it so awesome for me was the fact that I gave the Leafs no chance to win it. What made it sweeter for Lanny was that he struggled most of the season. Coming up with the winning goal was an emotional moment.
1967 - Leafs vs. Habs for the Cup
The series was the perfect Cinderella story. Everyone was making fun of the old farts. The Leafs had the oldest team in the League, led by their goaltending tandem of Bower and Sawchuk. Terry Sawchuck was 38 years old. Johnny Bower was 42. Red Kelly being changed from a defenceman into a centre was bad enough, but he was also in his forties. Watching these underdogs defeat the untouchables was priceless. Dave Keon was in his prime leading the Leafs in scoring in the regular season, and he was the leader of the Leafs in the playoffs. Dave Keon was the MVP and recipient of the Conn Smyth trophy.
Dougie Gilmour Playoff Goal vs. Blues
A fantastic game played between two equally-matched teams. The highlight was a goaltender battle between Curtis Joesph and Felix Potvin. Curtis Joseph was not human that game, facing 60 shots in the double overtime loss of 2-1. Gilmour made dipsy-doodle from behind the net and Joesph could not recover in time for the winning goal.
I have plenty more, but those are my best moments as a Leaf fan.