My high school best friend's family won. We were at college at the time, and I had lent her some money to go on an overseas trip with one of her courses. She met me at the pub with all the cash, and then told me the news. They won over a million pounds - it was the UK National Lottery jackpot.
They moved to Wales, and bought a big house and nice car. They also paid for our student house when we were at uni (I shared with my friend), which was very kind of them.
I always figure that because I know someone who won then that means I will never win! (Plus the whole not buying a ticket thing...)