I entered one in my guild's show last year as well as another local guild's show. It didn't win anything, and yes, I was concerned about how I'd feel if it didn't, but I got some great feedback on it, and I was very proud of myself for having the courage to enter it!!!
I say, go for it, and enjoy seeing it in the fair! Win or lose, you KNOW it's already a winner where it's most important!!!!!