T.O.D.
Back in the 80s, one of the Seattle radio stations used to give away sets of tickets to a lot of the touring productions at the the 5th Avenue Theatre. Apparently not very many Broadway trivia fans listened to that station between 6 and 7:00 a.m., so I used to win at will. Unfortunately, the tickets were usually for a Tuesday or Wednesday evening, and I was alway in rehearsals for some show.
I won a tennis racket and a can of balls at the YMCA when I was about 12.
I won a set of children's encyclopedia when I was a kid.
I have won several small jackpots on lottery tickets over the years.
Oh, and I won a lot of wonderful friends when I found Haines His Way, plus a couple of sparkling prizes.