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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
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4
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
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5
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
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6
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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7
When you fist a girl anally and vaginally hold her above your head like a trophy and shake her up and down as if you won the Stanley cup
She got a concussion from the Stanley cup I gave her last night
by LJA9107 December 02, 2017
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