Are we talking Prime Rape Tyson vs Prime Cokehead Chuck? Tyson was a well known street fighter, local gangsters and drug dealers didn't fuck with him and the one time someone did, Mike destroyed him in the street and thought he was dead.
The only way I see Chuck winning is if it went to the ground and Chuck took his back OR Chuck just kept his distance and threw a fuck ton of leg kicks. Prime Tyson was so fucking fast and had plenty of experience and knowledge fighting bigger guys with longer reach. Don't forget this guy bit someone's fucking ear off in a regulated match, what do you think he'd do in a street fight?