I'd have to go with Calzaghe. You'd basically be getting slapped silly (with a few power punches mixed in) buy some grinning ****er who doesn't slow down and when you catch him with a good shot he doesn't stay hit. And all though the fight you'd be thinking "I'll getting beaten by a guy who has the fighting style like a schoolkid"
I think the way Dirrell was against Froch You know you are much better, faster, sharper, much better footwork. Against a slow lumbering guy with B level skills and A level heart. Yet you still cant clearly outpoint the guy. Winky just because you can hardly land a damn shot through that guard, then he jabs you to death all night.
A welterweight going in against Tommy Hearns must have had his stomach in knots walking into the ring. I mean, what could you do? You couldn't outspeed him. You couldn't outbox him. He has height and reach on you. He has freakish power and is tremendously accurate. The only thing you can do is try to march through his firepower and get to him, which only 1 welterweight (Ray Leonard) managed to do and it took Leonard 14 rounds. Most of his opponents must have gone into the ring thinking "I am so ****ed."
bernard hopkins his refusal to slug and just box at pretty much the same pace through out the fight it would get to me
wladimir klitschko right now, you know he has a shaky chin, but you can't touch it, and if he hit you clean it's out
Herbie Hide. You swing a half hearted punch that you think missed but look down to see him on the floor. You'd end up thinking "the **** did I bother training for".
Hopkins and Calzaghe. When they fought each other it must have been a nightmare for both men. They cancelled each other out.
Floyd Mayweather. He does not hit that hard, is not extremely fast, not tall, is not a muscled freak, nor is he such a slick boxer that you can't land anything on him. You will THINK there is a chance at winning but then slowly come to realization in that last round..."He pimped me"
A prime Roy Jones...in some of his fights he really played with his opponents. This must be very frustrating.