I won a trip to Rome two Novembers ago. It's too bad that Rome is one of my most disliked cities in the world. But can't complain about the price! Oh and the spending money. And to cancel that the free side-trip to Florence was grand. I absolutely loved going there a second time.
Edit: Oh and back in Grade 9, I won $10,000 in cash and prizes off a TV call-in game show on YTV called Destructo Brothers Loot.
Edit: Oh yah and a bike at the Shriners Circus when I was even younger, and another bike from Toon-IN on RDTV.
Other than that nadda