Goblin Game Gatherer ruling states:

"When it comes to choice of items, use common sense. Items should be small enough to hide but large enough to count. Make it clear what kind of object you are hiding beforehand. For example, one player may choose coins and the other may choose dice. If you can't find something convenient to hide, write numbers on a piece of paper and reveal the numbers. Make sure the numbers are unambiguous (for example, underline a 6 or 9 so it can't be misread)."

(emphasis mine)

Lets say Player A chooses to hide Dollars. Player B decides to hide shoes.

Player B hides 2 shoes and Player A hides a 100$ bill.

When it is revealed, who wins?

I am inclined to say that Player B wins because he has hidden 2 OBJECTS, but an argument has been made that the 100$ bill is 100 actual DOLLARS, in which Player A has hidden.

Like I said, I'm inclined to say Player B, but I would like confirmation.

Silly? Yes. Relevant? In my EDH League it is.

Thanks in advance.

This is something the members of your EDH League need to hash out for themselves; the game rules are not going to help you.

As the ruling you quoted says, when playing Goblin Game you should use common sense, including having each player make their choice clear and unambiguous. Someone making unclear choices is a communication problem, not a rules problem.