My biggest bet to date was $2,500 earlier this year on Man United against Derby in the EPL. Had Man United laying 2.5 goals. Man U was up 3-0 until Derby got their first away goal in the EPL to cut the lead to 3-1. In injury time, Derby took down C. Ronaldo in the penalty area, and he got rewarded the penalty which he scored. Game ended 4-1 so i won my bet and increased my bank roll significantly, but I will never bet more than a dime per game. That taught me my lesson, as I remember sweating that sucker out.