Since my mind isn't functioning too well (finals week), I'll post the obvious:
The Most Awesome Administrator Award: Brandon Martus. (Hey, it's easy when there's only one!)
The Shortest Administrator Award: Brandon Martus. (See above.)
The Most-Fun-To-Toss-Around-At-A-Championship Award: Eugenia Gabrielov
The Most-Fun-To-Spotlight-Horribly-Out-Of-Context Award: Andy Baker
The -infinity Award (for being more creative in their reaction to receiving a score of -infinity in the caption contest): Heidi Foster (who has
claimed her award already)
The Most-Loved-Yet-Most-Irritating Poster: Dave Lavery (hey, when every word you say could be a game hint, reading your posts can get irritating, too!)
That's all I can think of for now.