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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It weighs just 34 pounds, but takes a team of 20+ men to lift it.
by howlincoyote2k1 October 27, 2010
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The act of holding a female above your head in Stanley Cup fashion after engaging in intercourse with her. After NHL players win the Stanley Cup, each player holds and kisses The Cup in a specific, triumphant manor. This may be achieved by inserting your left middle and ring finger into the female's mouth, inserting your right middle and ring finger into her vagina, hoisting her above your head, lowering her to your mouth and kissing her stomach.

Origin: University of Delaware, 2011
"Bro, I just Stanley Cupped that tiny bitch."

"Bro, I just Stanley Cupped that huge bitch."

"I felt like a winner after Stanley Cupping that bitch."
by technoruss June 12, 2012
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out of all the sports championships in the world...the stanley cup is the hardest to win. players must be in excellent physical and mental condition. Teams must advance through 4 grueling best-of-seven rounds to win the ultimate prize
the stanley cup is awarded to the winners of the playoffs. hockey fuckin rules.
by ted sells June 25, 2006
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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 01, 2017
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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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