My DH is the lucky one in this family - He's won tickets to:
Seinfeld
Blue Man Group
Larry the Cable Guy
Jeff Foxworthy
BB King
Jonny Lang
David Spade (we sold those)
Passes for the amusement park at Mall of America
Plus other things that I can't remember right now.
We joke that the only way we get a date night is by him winning stuff off the radio.
Plus lots of gift certificates to restaurants, a computer monitor, an air compressor, shocks for his Jeep...
Our DS won lunch with our city's fire chief at a school raffle last month. (He insisted on putting all his tickets in this bucket, which found funny because the fire chief is a friend of ours - we eat dinner with him every Wednesday night, we've gone to the Wisconsin Dells with him, his family, and other friends the last two years, and we're going to Disney with him, his family, and other friends in August - how many kids at his school can say they're going to Disney with the fire chief?!)
I used to be lucky, winning tickets to a few concerts and Stomp, but my lucky streak dried up a few years ago. I finally won something last month - a free night's stay at any Hyatt. Guess where we're staying the night before we fly out?! PERFECT!