When I was 9, in my first year at boarding school, I won the dormitory prize for tidiest bed-making - it was a bar of chocolate.
When I was 14, I won £25 (current equivalent, ~$750, I guess) from Pfizer, who gave it to the school to award to the most promising science pupil.
When I was 17, I got the highest mark awarded that year in any class in the Kent Music Festival, for my performance of Grieg's piano piece 'To the Spring'. But another boy got his picture in the paper, not me, because he'd won several classes - boo, chiz!
Since then it's been all downhill, through I did win a free dinner for two in the raffle at my work's Christmas do two years ago.