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Contests that I've won:

Contest(1st grade): Guess then number of candy hearts in the jar.
Prize: The jar of candy hearts.

Contest(3rd to 5th grade): Numerous elementary school art class drawings.
Prize: Many, 2 of my drawings were chosen along with others to be painted in in girl's bathrooms; 1 was chosen along with others to be put on the cover of the year's student directory; 1 was chosen to be framed and hung in the school's office.

Contest(8th grade): Rockey Mt. Poetry contest. My "21" poem about alcohol was chosen to be in the top ten of middle school poems.
Prize: Poem got published in a book, I got 2 copies of the book, and $40 given as a $20 check and told to put it in a savings account and have the interest grow it to $40.

Contest: Kung Fu Magazine Jackie Chan question trivia contest.
Prize: A Jackie Chan movie on VHS. In my case, it was Crime Story.

Contest: Raffle for Ping Pong Club.
Prize: The movie Grind on DVD.

Contest: Cheetos chips.
Prize: Pokemon Gold for the gameboy color. luckily I got a gameboy color recently.

Contest: Oroweat Bread.
Prize: 3 Colorado Rockies bobble heads.

Contest: Dragonballz.com.
Prize: Got 1st prize which was a DBZ movie poster, and a started deck for the trading card game.

Contest: Powerade Instant win game
Prize: A Powerade watch. It was a crap piece of plastic.

Contest: Raffle at a neighbor's birthday party.
Prize: A mini hotshots basketball game.

Contest: Raffle at a Chinese new year party.
Prize: A tube of 3 tennis balls.

Contest: Fast food game pieces.
Prize: Numerous coupons for free food, but I rarely used them.

Contest: Paper Airplane contest in the Quad.
Prize: For longest flight in the air, I got to pick out some walkie talkies.