3rd place at a bake sale when I was about 10. Ironically, it was pointed out to me later that the cookies I made were no-bake, so I won an award at a bake sale when I baked nothing.
1st place for Watermelon seed spitting (accuracy) at state fair when I was about 11 or 12.
1st place for Watermelon seed spitting (distance) at county fair the following year.
Nominated "most spirited" (our school's equivalent of "class clown") my senior year, but I ended up coming in 2nd to one of the "cool kids". He later came to me and told me that I "deserved" it more than he did.
What crazy awards have you received in the past?