If you go by "logic" which doesn't play very well into the fight game.
Rampage beat Liddell
and Silva ruined Rampages shit like two or three times.
I'd say that Silva could be Liddell on a BAD day hahaha. Silva is not to be fucked with. It takes a lot to get the nick name Axe Murder in a sport with no weapons other than yourself.
Otherwise I'd say that they match up fairly well because they both have an almost unorthodox fighting style and people used to say that Silva had a suspect chin (which is a dumb assumption) and if anybody can find the button it's probably Chuck.
I still think Chuck would get his shit ruined. But they would match up pretty well.
Though again, they said that Sakuraba would be a great matchup for Silva (though he is a BJJ black belt I believe...he is primarily a standup fighter(KNEES!!)). But goddamn he would run through Sak like he fought in KOTC or something.
A good matchup for Silva would be someone from his own camp like Shogun.