4 Astros tickets on 2 occasions. 2 Rockets tickets on 2 occasions. THAT close to winning 2 Super Bowl tickets one year for getting through 4 rounds of trivia (which no one had made it through after many tries), progressively harder...and I was only about 15! I can be proud of it.. but I was pissed back then. One of the answers was Napoleon Kaufman..
Last year, I won a Yao Ming autographed basketball from SR610 during the NBA Draft. It was some trivia question about how 5 Rockets draft picks have played in the All-Star game, or something like that, and they gave 3 and the first person to email with the other 2 won. I actually still haven't seen it -- my brother went to get it for me, and it's at my folks' house somewhere. Next time I'm in Houston, I'll have to go find it. I also won tickets to the Academy National Invitational a few years ago. It was pretty cool -- great games!
Tickets to: Sold-out Arcade Fire (sucked because they were at Mary Jane's) Ben Lee (sucked because he was at Mary Jane's and he's Ben Lee)
Back when I was in high school, the morning radio show I would listen to played 2 songs on top of each other at the same time and you had to call in and name both songs and the artists, which I found to be pretty easy. You could only win every 30 days, so I'd call in once a month and get a free CD. Probably won about 10 CDs that way. The cool thing about it was that it was a certificate for ANY CD new or used you could find at the CD Warehouse where I lived. Not some random crappy band they had some CDs of. Haha, also one time I think I won a certificate for a dozen donuts for answering some random trivia question on the radio.
I flamed out on Matt Jackson's show like 4 years ago on one contest. Ran the table with 6 of the 7 nicknames he gave me. I choked on "Reign/Rain"-Man.
I won tickets to see Jane's Addiction a couple of years ago at Verizon from the Buzz and got to see them backstage before the show where they performed a mini-concert backstage in front of me and about 20 other contest winners. It was bad ass. I also won tickets to see Saul Williams at the Engine Room from KPFT. He's a spoken-word artist that had a band backing him up. It was really enjoyable, much better than I expected.