Why couldn't the headless horseman win the race?

He couldn't get a head.

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Win Jokes More Win Jokes

What do you call a crowd of chess players bragging about their wins in a hotel lobby?

Chess nuts boasting in an open foyer.

What does a Maple Leads fan do after his team wins the Stanley Cup?

He turns off his Xbox and goes back to bed.

Race Jokes More Race Jokes

Who won the race?

Society.

What do you call an alligator that wins a race?

A chompion. (7-year old me thought he was very clever.)

Head Jokes More Head Jokes

How can you tell if a shark has dandruff?

He left his head and shoulders on the beach.

Why did Tigger stick his head in the toilet?

He was looking for Pooh. - *My little brother told me this one hit me with a little bit of nostalgia.*

Headless Horseman Jokes More Headless Horseman Jokes

Why couldn't the headless horseman win the race?

He couldn't get a head.

Why was the Headless Horseman depressed?

He could never seem to get ahead in life.