My worst loss was experienced when I still do buy games.
I bought this games from a Facebook user for $100 comprising of a 4:0 correct score and a straight win. I combined them and failed to play the 4:0 single, but I played the straight win single because I thought it had more chances to come through, long story cut short, the correct score came through and the straight win messed the ticket up. What angered me the most was that if I had singled out the correct score, I would've won a lot of money since the odds were over 50, but I lost everything which amounted to almost $150. Since then, I don't think I have ever bought games again, I was really heartbroken.