I will never forget this one...this was back in the old WSEX days.
You could buy shares in a game live. Each share that was in the money at the end of the game was worth $100. I cant remember the teams at all, but I remember the spread was visiting team +5 and the score was like 24 14 with like 45 seconds left, home team had just scored to go up by 10. I buy like 15 shares of the visiting team for like $8 each and sure enough the visiting team goes down and scores with like 2 seconds left. I am estatic, just won 1.4k basically.
So the visiting team onsides kicks....right in the arms of a defender who runs it back untouched to ruin my cover. It was a pro game, right about year 2000 - that was a tough one.