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Gonzaga tried taking him down a fair number of times in their match and got him down once or twice, but he didn't stay down long. He displayed a rather pretty sprawl in that one, did Stipe. But Gonzaga isn't exactly a wrestling specialist now is he.
Beltran got him down once (overbalancing him after Miocic threw a knee) and kept him down with some gnp for maybe 15 seconds. JDS did a gorgeous trip and had Stipe on the mat for a whopping half a minute. But neither is a patch on Cain when it comes to the Grind.
So yeah, this would be a very interesting experiment.
Cain will take him down.. not sure if he keeps him down but he will go down many many times and cardio will decide that fight.