Lucky to push top 20? I would say Dent would be lucky to break the top 200.
It is a huge step up for George... he might win, anything can happen, but it is just about the worst possible matchup for George (not considering guys like BJ of course). Joe is another top control specialist, a bjj blackbelt, with better hands (IMO).
He might win his bets, but I supect he is going to continue his losing streak here. Wand and Sosz are ok (I made the Sosz play myself). But I would not be surprised at all to see Bisping win. He is forgetting the takedown, which I think Bisping will use a lot, after finding success with it against Kang.