Of the ones I'm familiar with I would say the dirtiest were Ali, Marciano and Holyfield. Ali's holding and hitting and neck yanking are legendary. You can see it in almost every fight. Marciano- Hitting after the bell, hitting on the break and rabbit punching. One or two cases of hitting a man while he's down on one knee. Holyfield- Head butting. Liston- Doped gloves? I don't believe Clay's claim that Liston blinded him with doped gloves in their first fight. I think it was staged. Machen made the same accusation against Liston. It may have been true. Machen had more credibility than Clay.
Ali is one of the dirtiest ever. Lennox had his dirtier moments. Wladimir also sometimes. Though both don't do it quite as often as Clay.
Holmes...all thumbs Marciano (accidental elbows) Lennox Lewis ..hold & Hit ) and rubbing corn rows Evander (head) Ali head pull downs
1. Mike Tyson 2. Frank Bruno 3. William Harrisson 4. Muhammad Ali / Cautious Play 5. Rocco Markegiano 6. Lawrence Holmes 7. Lennox Lewis 8. Riddick Bowe 9. Evan Fields 10. Wladimir Klitschko 11. Tim Witherspoon Tyson's butting which was harmful wins him de argument over Ali's whose fouling was usually less harmful yet still decisive in its effect . Going more by what i read , because i did not notice it vs Cream and i watched Charles #1 years ago and not sure that entirely because it was extremely disgusting and boring fight 2 watch , Markegiano was by far less dirty than Tyson but ppl usually claim that he was somewhat similar in cheating as well . Holmes thumbed Holyfield and Shavers in their 2nd fight , Ali thumbed Terrell and who knows who else ? Fields' butting i believe was more due 2 his style and defense than intentional , but i do not ignore de outcomes . Wladimir got penalized a pt in Germany vs Haye . Lewis blatantly cheated vs Grant . Witherspoon blatantly cheated against Bruno , whom is a yet better mention , a serial hold and rabbit punch .
No mention of Dempsey? Rabbit punches, low blows galore! Although the thing with him and Marciano is I don't think they went out of their way to be dirty it was more just their way of fighting as Archie Moore said "slam, bam, didn't give a damn". Holyfield and Tyson were dirty very much on purpose particularly I think Tyson, who I remember (4got which fight) being in clinches and repeatedly elbowing and butting.
I have to strongly disagree on that, Tyson was clean fighter. If he knew how to fight dirty, he would not have had to openly ear bite Holyfield.
Marciano was rough, not dirty. He had worse stuff happen to him, Walcott fight he got foreign substance in eyes, and Walcott pulled some dirty move on him. In second fight with Ezzard Charles, he caught elbow to nose that ripped it open. Dempsey fought a bit dirty, but so did everyone else then, maybe he just did it better?