For getting second place in a coloring contest, I won two tickets to see the Wizard of Oz, and $10.00, and in those days popcorn was only 15¢.
However, mom helped me, and I always felt guilty about winning. Haven't won anything since, except last years YorkieTalk raffle and I won a beautiful painting of a Yorkie by Yorkie Painter. I find it ironic that my only two winnings involved art.
Oh my goodness, I just remembered I did win $250.00 once in Vegas, and bought a painting with my winnings.