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1.
A slang term meaning to bet on horse racing.
"Im gonna head down to OTB. You wanna come?" - Gambling Degenerate

"No thanks. Why do you piss your money away playing the ponies?" -Smart Friend
από dmb7211 5 Ιούνιος 2010
 
2.
This phrase is actually a mistake. Instead, one should say "playing the horses". Playing the Ponies is something small boys would say.
Eric received a text message that the ponies were loose and used an incorrect sentence involving playing the ponies.
από death row 25 Μάρτιος 2011