Like I say, I rarely bet (unless you count lottery, which I get each week, one for our national Lotto and one for the Euromillions; haven't won yet. Think I keep getting broken tickets) but my biggest bet and claim to fame/shame was years ago when I bet AGAINST Ireland, World Cup qualifier I think, who were losing 5-1 to Cyprus. I noticed live betting was still active and 5-2 was something like 250-1! I said **** it I'll do it, Cyprus scored again and I was quids in!
Except that the online system refused to complete my bet. Luckily I had been talking to a rep on the phone at the time and told him I wanted to place the bet but it wouldn't go through. Long story short, after a lot of arguing they gave me half my winnings (as technically my bet had not gone through and they could have given me nothing) so instead of 800 Euro I got 400, but it bought me a new fridge freezer.
For a long time I felt a mixture of triumph and shame every time I opened the door of that thing...