I hate to say this, but I've won lots of things except the lottery.
My husband and daughter don't win, but my son wins, too.
I guess the biggest prize I've won was a week in a condo in Maui and $1100 for airfare. It was a raffle at our daughter's grade school for the annual parents' party fundraiser. The father of one of the mothers owns the condo and donated the week. The rather affluent friends of the mom chipped in the money. The raffle tickets were $25 5 for $100. I had my own consulting business then, so I bought 5 and wrote it off.
The raffle was one where they draw numbers and you are in the running if your number isn't picked. You also had to be present to win. The party ended at midnight. At 11, I still had 3 good tickets. They were down to the last 3 and 1 had left. I won.
The best thing Ben won was also a raffle at the same school. They sell wrapping paper every year. Anyone who sold wrapping paper was eligible to win a boom box. Ben won.
Did I mention that I always find 4-leaf clovers? Even on the Isle of Skye in Scotland?