Most I ever found on the ground - $80 when I was 17 years old. Was with my sister in the city and being kids and not having any money this was the best especially because everything was so cheap back then - $7.50 movies, $4.50 meals at mcdonalds, $1 cost of public transport ... everything is 300% more expensive than back then (And it sucks!)
Most I ever won - A pub used to have a competition where you write your name and enter it and they will draw it weekly and winner gets 2 free tickets to AFL (Aussie rules). I won this twice in a row before they pulled the competition - obviously I was the only one entering