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Pony
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For more on marking an answer as the "Best Answer", please visit our FAQ.The term has been around since the late 18th century, apparently. The first paper rupees appeared around 1770 (I don't know if they had a pony on them), but I find the link a bit tenuous. "Origin unknow" is probably the best we can do. See World Wide Words.
From The Word Detective, a US columnist and web site, answering a question about "pony keg" and "pony up."
The nice thing about your question is that both the uses of "pony" you ask about come from the basic sense of "pony" as "a small horse." A pony, strictly speaking, is a small breed of horse, rather than simply a young horse, which is called a "foal." The root of "pony" was the Latin "pullus," meaning any young animal (which is still with us in the form "pullet," meaning a young chicken). "Pullus" became the Old French "poulain" (foal), whence came the diminutive "poulenet," which then trotted over to Scotland and showed up as "powney," which was later Anglicized to "pony."
"To pony up" and "pony keg" both embody the "smallness" aspect of "pony." "Pony" has meant a small amount of money since the late 1700's, when it specifically meant the sum of twenty-five pounds sterling (which was actually a hefty hunk of change at the time, but go figure). "Pony kegs," popular at fraternity parties and the like, are smaller than standard tavern-sized kegs, by analogy to a "pony" of liquor, which has meant a small glass of spirits since the mid-1800's.