Top Definition
The holy grail in hockey, the champion of the NHL gets it and their names on it also, the best trophy in sports.
It was a great day when Ray Bourque hoisted the Stanley Cup.
by cardinal_fan October 21, 2004
It weighs just 34 pounds, but takes a team of 20+ men to lift it.
The Chicago Blackhawks won the Stanley Cup in 2010.
by howlincoyote2k1 October 27, 2010
Hockey's Holy Grail.
Jordan: When I grow up I'm going to win the Stanley Cup!
by natalie298755 October 09, 2009
in connection with sexual intercourse the proverbial "Stanley Cup" is a Game within a mostly lesbian sexual act called Canada's History involving maple syrup as a lubricant. The winner of the "Stanley Cup" reiceves oral pleasuring from the losing parties.
Girl 1:
Why was Susan in such a good mood today?

Girl 2:
When we studied Canada's History last night Susan won the Stanley Cup and therefore we had to eat her out while licking all of the maple syrup off her cunt.
by LittleStevieC February 06, 2010
When a guy catches his own fart in his hand, and then gifts it to the face of his unsuspecting girlfriend or wife. Contrast with Buttercup, which is when the lucky guy gets the same treatment from his girl; she catches one of her own and gifts it to his face (a rarely performed but incredibly beautiful courting ritual).
Paul tenderly gave Sheila a Stanley Cup for their anniversary, catching his excrescence in his hand and covering her sleeping face until her eyes slowly opened wide in realization of his wonderfully thoughtful gift.
by WhizzerWhite January 18, 2009
Honestly, the ugliest and most exaggerated trophy in all of sports. Unlike all other trophies, you would not know this is the championship cup for hockey if you looked at it. It looks more like an artifact that belongs in a church to represent the Holy Grail.

It got its name from its creator, a guy named the Lord Stanley of Preston, who was governor of Canada at the time. He bought a decorative punch bowl (Yes, a punch bowl) and made it the trophy. He had the words "Dominion Hockey Challenge Cup" engraved on one side of the outside rim, and "From Stanley of Preston" on the other side.
Person 1: What the hell is this sport, and what the hell is that massive thing he's carrying over his head?

Person 2: It's hockey, and that's the Stanley Cup they win as champions.

Person 1: Dear God...
by Trip'n June 22, 2010
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