Roger blasts him. If they fought 10 times, Bailey might catch Roger and put him to sleep twice. The other 8 times, Roger beats the shit outta him and stops him.
The chin-punch ratio here doesn't allow me to say Roger wins easily. I'd pick him, but it's a tightrope walk the whole way.
I'd pick Roger without hesitation... Bailey might win one out of 10... He simply does not have the presence of mind to deal with a boxer of Roger's quality and Roger's own considerable power would force him to be even more careful... He's just not good enough. He's got a one in 10, out of nowhere chance.