wouldn't you know who won the pony

refers to the story told by Jim Cornette when a local wrestling promoter , faced with declining attendance , rigged a lottery to give a way a pony so his son won it , so we did not lose money on the deal . As a result anything is is obviously rigged is referred to as wouldn't you know who won the pony .

Billy got picked to be hall monitor again .
Well Wouldn't you know who won the pony

wouldn't you know who won the pony by BellasaurusTheJust July 21, 2019

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Wouldn't you know who won the pony

Implies that the previously stated is rigged; local wrestling promoter, as told by Jim Cornette, gave away a pony to increase ticket sales and, to avoid losing money, rigged the raffle to ensure his son would win the pony

Of course, that asshole was late again!
Oh, wouldn't you know who won the pony!

Wouldn't you know who won the pony by Jack_Bongos January 15, 2020

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for the girl who won’t give me kisses

use when you’re giving something such as a playlist or something you put some thought into to a female who won’t really give you the time of day but you’re still gonna risk looking stupid cause she’s that cool

i made a playlist for the girl who won’t give me kisses

for the girl who won’t give me kisses by prodbybeastboy June 10, 2018