Crocop has faced guys as tall as Tim Sylvia before. Not too long ago he knocked out Fedor's brother (Aleksander Emelianenko) with a head kick. Aleksander is only 2" shorter than Sylvia, so from that fight we know he can kick to Tim's head level (but can he do it without telegraphing it?). Also, Aleksander is an excellent striker. However, Aleksander tends to take a lot more chances in his striking than Tim Sylvia will. Aleksander is willing to take a hit to give a hit, and that's what got him KO'd by Crocop.
http://youtube.com/watch?v=VCx5YT5RxXs. Sylvia won't do that.
Tim Sylvia will play it safe....very safe. Also, he's got one of the best cornermen in the MMA business, Pat Militech. Militech will keep Sylvia backing up and jabbing...waiting for Crocop to come in range and try to counter, throwing in a leg kick every now and then throwing the power hand every now and then (but not committing to it unless Crocop's in trouble). As long as Sylvia keeps his range and keeps Crocop off balance with the jab, it will be hard for Crocop to land any kicks at all. Even with just a leg kick, Sylvia has enough reach to tag him. Also, Crocop's chin is somewhat suspect. He got KO'd by Kevin Randelman, who's basically a wrestler, but was able to hang with one of the most powerful strikers in MMA, Mark Hunt. Sylvia definitely has the power to KO Crocop, but often he's hesitant to use it...he won't always let his power go for fear of missing and being off-balance.
Crocop will have to close the distance somehow, and that's where the chess game comes in. Will he try to wear down Sylvia with his powerful leg kicks or body kicks? He'll risk eating a jab with the leg kicks, a possibly a power punch with a kick to the body. Will he try to come forward no matter what, trying to time a shot over Sylvia's jab, which is often lazy? Crocop is a southpaw and Sylvia is a righty, which I think will be more awkward for Sylvia than it is for Crocop (because Mirko's used to it). Crocop is faster, a technically better striker, and has more weapons (both legs and both hands have crippling power) - if he can get Tim to mix it up, he can really hurt him.
Another possible strategy for Crocop is to circle and leg kick, circle and leg kick. Sylvia's left leg is gonna be sticking out there, because of the righty-lefty situation, and if you've seen the recent Crocop fight with Yoshida (
http://youtube.com/watch?v=4zo3i1AgoX0), he can win a fight just with leg kicks. Of course Sylvia's reach is so much longer than Yoshida's, so it's possible he can land a stiff punch after a Crocop leg kick. I think this is what Mirko will start out with. If he can get Sylvia to come forward to him or hurt his leg enough that he's changing his stance, then Crocop has basically won. If Sylvia can get Crocop to come into his "trap" or get Crocop to be impatient, that's how he'll win. Also, Crocop has to be careful if he hurts Sylvia. Mirko tends to jump quickly on an opponent when he thinks he's got him hurt - as we know from Sylvia/Arlovski II, that's a dangerous situation. Sylvia's got a great chin, and if he get Crocop to let down his guard a little bit, he can KO him.
Crocop is an all around better striker, more experienced, and just all-around a better fighter. Sylvia has the reach, a big right hand, and knows how to use both of those weapons almost perfectly. He's also going to come in with a great gameplan and cornerman, because of Militech. Militech will have him extremely well prepared. This could really go either way, but if I had to bet money, I'd bet on Crocop. I think it will all depend on who sticks to their gameplan the best. Sylvia has to make Crocop come to him, pepper him with jabs, and make him pay for missing (or even landing) a kick. Crocop has to wear down Sylvia with kicks, get Sylvia to brawl, or get Sylvia to come to him. It should be exciting.
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Also, on edit, you metioned Crocop/Fedor - one of the main reasons that Crocop went to the UFC is that Crocop thought Pride was jerking him around on getting a rematch with Fedor. I don't agree with him completely (it was due to injuries to both guys and them trying to have Fedor fight on American soil against an American, Coleman). The report from his camp is that Crocop would have remained with Pride (and taken less money) if he would have gotten another shot a Fedor in the next few months. Pride couldn't guarantee it and the UFC stepped in with a boatload of money (he got 350,000 for fighting Sanchez, and that doesn't count whether or not he got a % of the PPV sales). Crocop wants a rematch with Fedor badly, because he's now got a decent ground game and thinks he can beat him. Apparently Crocop thinks that he can go into the UFC, whip ass for his 6 fight contract, make himself a huge commodity as the UFC champ, and make his own terms with a fight with Fedor (UFC, Pride, Bodog, or otherwise).