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Stanley Cup Playoffs 

Mid-April through early June is a beautiful and magical time in the sports world. Playoff hockey is on and everyone can relish in it's majesty. The Stanley Cup playoffs are filled with parity, excitement, overtime games a plenty, and climaxes in the raising of Lord Stanley. Truly a must watch for anyone who enjoys hockey or sports in general
M: Hey man, the Stanley Cup Playoffs are on and the Nashville Predators take on the Colorado Avalanche
D: Hell yeah! And a little bit before the Washington Capitals take on the New York Islanders
M: I'll make the food
D: HELL YEAH! HOCKEY FOR LIFE!
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Stanley Cup

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.
Stanley Cup by LittleStevieC February 6, 2010

Stanley Cup

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.
Stanley Cup by WhizzerWhite April 12, 2009

Stanley Cup

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...
Stanley Cup by Trip'n June 24, 2010

Stanley Cup

A cup.. Normally anyways. In a certain school its definition has been rewritten to be : A deadly weapon to be used to commit blunt force trauma on the skull.
This kid said he wanted to fight me. Little does he know, i've got a Stanley Cup in my backpack waiting on him.
Stanley Cup by ndhoodquencher April 28, 2023

Stanley Cup

The new Yeti and Hydroflask. Every basic white chick has to have it. Overpriced cup that everyone wants for some reason.
White Chick: Have you seen the new Stanley Cups there so cute. Will you get me one, babe?

Babe: Are you kidding me? A stupid cup isn't worth that much!
Stanley Cup by Verity January 7, 2024

Stanley Cup

A cup that for some reason so many people want (thanks to TikTok, of course) that they literally camped outside of Target just to get this stupid cup. Oh, and by the way, these cups sold out in less than 4 minutes flat.
I got a Stanley cup because I waited outside of Target since 1:30am.
Stanley Cup by Pialinist January 25, 2024