Silliest thing I ever won was a huge, bright pink, stuffed elephant toy from a hospital charity raffle. It filled the back seat of the car, then because Mum was taken with it and wouldn't let me chuck it out it filled half the back room of the house for a couple of years. I finally talked her into redonating it. Then when it was gone I missed the damned thing.
I was often middling lucky on the poker machines, never lost much and often won enough to cover at least the costs of the night out. No big jackpots though, $240 was the best I did.
Won over 200 bottles of wine over a few years as trivia prizes. 8 on one night was my best effort. I'm allergic to grapes!

Gave them all away as 'bribes' to tradesmen and neighbours and other disgruntled trivia players, and Xmas presents to those who didn't know where they come from.
Things were better with the trivia raffles though, won just about every kitchen gadget at one time or other. Still using some of them. A can opener, and one is a toaster the size of a battle cruiser, 4 slicer. Really economical for one person, not. But it's around 15 years old and still as (not so good) as it ever was and I know where not to place the toast where it'll cremate now so I've kept it.
The last thing I won was a Lillipilly tree from the Rural Firey's raffle at the voting venue. They make a motza that day getting the voters coming for raffle tickets and going for a sausage sizzle.
I bought the ticket, dropped it into the debris in the bottom of the handbag and forgot about it until the fire engine whooped in the driveway and two grinning fireys dropped it off on the doorstep. It was festooned with $2 scratch lottery tickets threaded on a long ribbon. Spent an hour scratching those for the sum total win of 2 more free ones. siiiiiiigh.
I don't want the damned tree! I can't plant it! So I battle to keep it alive out of a sense of duty. Anyone want a Lillipilly tree?
Oh, and I received a 14c gold chain in the mail years ago. Total mystery until I remembered a newspaper coupon I'd sent in about 2 months previously.
That was a nicer than usual surprise. Only one I got though, others win Plasmas and cars with coupons but the chain was the only thing I got lucky with.
Still, haven't done too badly, can't complain about bein' a total loser.
