Who: Toronto Maple Leafs vs. Pittsburgh Penguins
Where: Maple Leaf Gardens
When: *shrug* Some time in the '90s
Final Score: I'm pretty sure TO won by a couple goals
At full disclosure, I really haven't been to that many NHL games, and none have been in the playoffs, but I wanted at least one pro game on the list, so this is kind of like the CHA/AH autobid of the list.
This one wasn't necessarily a fantastic or dramatic game--I'm not really sure a regular season NHL game could be given how long the season is--but it does crack the list for being one of the coolest hockey experiences of my life. I watched Hockey Night in Canada fairly religiously growing up, and the Leafs were my favorite NHL hockey team, so actually going to Maple Leaf Gardens was like going to Hockey Mecca.
I'm probably dating myself quite a bit with this, but the Leafs were a pretty good team, and tickets were hard to come by--the Leafs sold out every game at the Gardens for like 50 years. My dad and I were literally chased down the street by a scalper as someone tried to sell us their tickets.
There were a lot of great facets about the old Maple Leaf Gardens, and the place practically oozed history. I think my personal favorite quirk about the arena was that there was literally nothing separating the stands from the benches. The aisle behind each bench extended all the way onto the bench. Nowadays, I don't believe there is any professional rink where you can reach the bench from the stands. And what seems even weirder, there was no security--at least no visible security--blocking off the opening between the stands and the bench. I mean, if the Chicago White Sox' US Cellular Field had that, I'm pretty sure people would die. It's just one example of how when the Leafs moved to the shiny new Air Canada Centre, they gained some modern amenities, but lost some of the uniqueness that made their home arena so legendary.