The more I think about it, I'm changing my vote because it's a money game. If it were free, it wouldn't matter as much, but by putting up money (and it doesn't matter that it's "only" $100, the value is different to each individual) Michelangelo could demand these two games be graded as wins on the grounds of misleading wording, and it would be wrong to deny him that. If this were a huge contest like the Hilton, and there was wording in the rules that could be misinterpreted, that entrant would probably hire a lawyer and he would definitely win his case. Just saying. The way around this in the future would be to include in the rules "Management decisions are final".
But, in closing, Michelangelo posted the games prior to their start time (which is ONE of the two conflicting rules) so "legally" they should be allowed to stand as wins. I don't think you need a vote. It's pretty clear what the end result should be. The fault is in the wording, not the user, so I don't see how you can penalize the user.
I would suggest counting them as wins, cleaning up the wording, and move forward now that we all know the intention of the rules. Otherwise, call the contest and refund the money (which would be more of a mess).