As for the Topic of the Day....
When we lived in Connecticut, I was a regular winner of the radio contests on WRNL.  In fact, I had won so often at one point, that I was "banned" from calling in (and winning) for a period of six months.  I won various prizes: t-shirts, tickets to the county fair, tickets to see 
The Fantasticks (my parents used those), tickets to see The Village People (I didn't bother to pick up those - I was only nine at the time), etc., etc., etc.
I also used to win various raffles: house plants(!), store gift certificates, restaurant coupons.
Lottery-wise, I've had a few nice wins, well, at least enough to almost break even on all the money I've spent on playing the numbers over the years.  -Oh, and my Dad just won $100 on a scratcher!
I won a few of the contests that the Smithsonian website would have from time to time: a small hedgehog stuffed animal, and a window card for 
Rent.
I was the Grand Prize winner one year of MTI's own website contest.  They would post a clue in the form of a limerick, and you had to guess the name of the show and/or the character.  I won an autographed copy of one of Steven Suskin's books, as well as the 3-CD 
Most Happy Fella on Jay Records (which DR elmore assisted on/with).  -And I was the Grand Prize winner since I had won a number of the weekly contests throughout the year - thus, I had also won a couple of other OCRs - including two copies of 
Secrets Every Smart Traveller Should Know  
  
I also think I've won a Sparking Prize from this here website too.