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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

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 like to know?

A way of coyly flirting with someone. Yu can impress them with your secret knowledge
Guy: “I’m pretty good with my hands”
Girl: “Are you?”

Guy: “Well, wouldn’t you like to know? ;)”

wouldn't you like to know, weather boy? 

Very sketch sentence used bu juvenile delinquents to throw off reporters.
+Here's an actual customer out here, uh what's the best kind of firework to buy?

- Wouldn't you like to know, weather boy?

+Where are your parents? Kid's sketchy, back to you guys.

You'd like that, wouldn't you?

A response when someone uses the insult "Suck my dick, my balls etc."
person 1: I hate singing!
person 2: Cause you can't sing.
person 1: Suck my dick.
person 2: You'd like that, wouldn't you?

Oh you'd like that wouldn't you? 

If someone says fuck you say "Oh you'd like that wouldn't you". Then the person will regret it and you would've made them embarrassed and then you have won life.
Hey you wanna here a pussy joke?

Sure

Nvm you wouldn't get it

Fuck You

Oh you'd like that wouldn't you?

*embarrassed*