Machida UD. More weapons in his arsenal, faster, highly successful with his TDs and sweeps.. Expect a war like Liddell/Silva.
It'd be a great fight. Machida would land more due to superior speed, footwork, and straighter punches but he doesn't have the power or Chin to win a gunfight which Chuck could and probably would force. I could definitely see Machida's Glass Jaw shattering.
Funny thing is they sort of play into one another on paper. Chuck really loved to back up and wait for a mistake. Lyoto at his best really likes to change up angles and throw the sort of kicks and punches where he doesn't really, 'set.' Prime Chuck had a decent beard, I don't know enough about Machida's, he's a really hard guy to catch as it is and plenty dangerous with his overall game. For Chuck, vintage he would be cautious, wait for his opportunity and look to land something solid, then go for the kill as he did against opponents like Couture and others. Machida, I think his best bet is to be passive aggressive with a little more aggressive than normal to inflict damage but to avoid an all out exchange. He has the ability to pick Chuck apart. But then Chuck only needs to land one of his short punches to buzz anyone. I think either Machida would batter a prime Chuck for a few rounds before finally really catching him, or Chuck takes Machida out in one or two by simply catching him with a solid shot and finishing him. Really interesting match if you ask me. A lot depends on how well the guys time one another, Chuck was really good at this in his prime.
When Liddell fought Franklin, I thought, "Wow, Liddell can do everything." Liddell ended up ko'd in that fight, but that is beside the point. The point is Liddell could have excelled in numerous areas, but he ultimately fell in love with one particular style. The Liddell that attacked Franklin with punches, kicks, and take downs never existed in Liddell's peak years. I think that a prime Liddell against Machida would find himself in a slightly worse predicament than the just past prime Liddell faced against Jardine. Machida by ud.
I think it'd actually be a pretty boring fight. Both fighters like to sit back and counterpunch, so it'd probably not have much action. A lot of people seem to awesome that Machida would be able to confuse Liddell standing but its worth remembering that Liddell's original striking discipline was actually karate, so he may be better at reading Machida than others.
Prime Iceman has too much power for Machida. He was also fast back then with a cast iron chin. See his fight against Guy Mezger in Pride for an example. Mezger had more tools in his arsenal and was arguably faster. Liddell eventually found his range and walked him down with one of the most brutal right hand KO's you'll ever see.
My thoughts exactly. Imagine if Liddell fought his whole career like he did against Franklin. Obvioulsy a little less wild and open but punches, kicks, takedowns the lot. You wouldn't be wrong for thinking Liddell was a boxer but the guy was a good kickboxer with good wrestling! What a combination if you can add good hands, which he did.