On honeymoon in Tenerife I "won" a prize on a scratchcard from an insistent timeshare seller. Coincidentally he won the offer of a "punch in the teeth" if he didn't fook off.
Absolutely true story....
My mum used to work in the bookshop in North Street (Websters?), they had a woman come in one day and ask for "The book about dinosaur words" for her son. They all looked puzzled but she pulled out a piece of paper and written on it was "Roger the Saurus"
I won a comp on Absolute Radio, £250, 2x IoW festival tickets and a DAB radio. Ebayed the radio & tickets.
I also won £500 in the St Wilfred's hospice lottery in the third month I'd been in it.
Oh, and a "wheelbarrow full of booze" at Jevington fete 3 or 4 years back, many bottles of wine...