Yes, with Mitch “Blood” Green. Tyson broke his hand on Green’s face, and didn’t even knock him down.
What David Simmons said and many martial artists repeat - hard target, soft weapon. Soft target, hard weapon.
Regards,
Shodan
"His famous one inch punch was dependent on speed and not mass to generate power; he was able to accelerate his hand to an extreme velocity almost instaneously and thereby generate an extreme amount of force. "
Speaking as a martial artist of several years…
Not exactly. Speed has very little to do with it, the one inch punch is almost entirely based on leverage and alignment. It is about creating momentum in your body which transfers through to your punch. In isolation, hand speed is not a factor.
For example, it is possible to do the one inch punch as a “zero inch” punch, where you start with your fist already resting on your target. The coiling force and weight shift of your body transfers all of the force necessary to send your opponent flying backwards. Your fist hardly travels at all.
If Bruce Lee tried a one-inch punch while standing on a skateboard, it would be extremely ineffective. But when able to use the leverage of his body against the vertical vector (the ground) as well as the horizontal vector (friction) he develops an immense amount of force.
Shodan, I did find a cite that said Green was “knocked cold” but that could easily be hyperbole, I mean, it came from his lawyer for Og’s sake 
From the AP, FWIW. Eh, either way, the dude was messed up.