Biggest thing I won was a Second Chance Drawing from the CA Lottery NBA Scratchers. I got R/T Airfare for two to any NBA game ( I'm a Laker fan so I choose to see them play the NY Knicks in NY ) Hotel paid for 2 nights, 2 Tix to the Game ( I got to choose where I sat ) 2 Lakers Gift Sets ( 2 Jersey's, 2 Shirts, a clock, a travel bag and a Golf umbrella ) as well as $1800 cash.
Total Gift prize was $4200
Years back I used to gamble online. I won $1200 on a $2 slot
I've won Concert Tix from Radio Stations
2 Xmas's ago my wife won $2500 on a $3 scratcher X-Mas night