I have never won much...
most money I ever won was 20 krones, from those lottery cards you scrape w a coin. I've won 20 krones a few times...
In slot machines my record is 7 krones.
I've won some board games. Like... monopoly...
I was among the winners in a elementary school-wide traffic design competition once, and had my idea implemented: A long, tall dividing wall, shielding residential areas from the noise and smoke from the nearby freeway. Originally, that was not my idea, as I intended the separation wall to divide the world in two: Humanity in small pockets, walled in, to prevent more harm to be done on nature.
But I was proud enough anyway.
I won a bicycle helmet, and I got to pose with the other winners.
I am the only jackass on the photo with the helmet on the wrong way.