I know it might be a bit early to start thinking about the next fights after UFC 100 for Brock Lesnar, Frank Mir, Georges St-Pierre, Thiago Alves, Dan Henderson, and Michael Bisping, but let's go for it anyway.
I will rank the three possible fights, in order of possibility, and then listing any dark horses.
This article is not about predictions for UFC 100, so I will look at the possible fights for if the fighter wins and loses.
First, let's start with the main event. And let's go age before beauty (so to speak) and start with Brock Lesnar.
If Brock Lesnar wins
First choice: Brock Lesnar versus Shane Carwin would be the battle of the most powerful new generation of heavyweights. UFC 107.
Second choice: Brock Lesnar versus Nog—the man who dishes out punishment with his "lunchbox hands" against the man that eats punishment for breakfast. This would be more marketable than a rematch with Couture, so therefore, it goes above Brock versus Velasquez. UFC 106.
Third choice: Brock Lesnar versus Cain Velasquez. I doubt the UFC would put Velasquez in against Brock so soon in his career, and they will most likely give him a few more fights against easier competition. UFC 107.
Dark Horses: Brock versus Fedor (fingers crossed.) UFC 107, Brock versus Junior Dos Santos UFC 108. Brock Lesnar versus Mirko Cro Cop. UFC 108
If Lesnar loses
First choice: Brock Lesnar versus Gabriel Gonzaga. Gonzaga seems to be the gatekeeper of the heavyweight division, and a likely opponent for Brock if he loses. UFC 107.
Second choice: Brock Lesnar versus Mirko Cro Cop/Junior Dos Santos. He could fight the winner for a No. 1 contendership. UFC 109.
Third choice: Brock Lesnar versus Cheik Kongo. Kongo is so inconsistent that it seems he would be a lamb to the slaughter against Brock. UFC 106.
If Frank Mir wins
First choice: Frank Mir versus Randy Couture. I only put this match ahead of Mir versus Carwin because Couture is more marketable than Carwin, but this fight depends on the result of Nog versus Couture. UFC 107.
Second choice: Frank Mir versus Shane Carwin. Carwin, if he wins, will be the No. 1 contender. And at the moment, I think he will beat Velasquez. UFC 108 or 109.
Third choice: Frank Mir versus Cain Velasquez. UFC 108 or UFC 109.
Dark Horses: Mir versus Fedor, Mir versus Mirko Cro Cop, Mir versus Nog.
If Mir loses
First choice: Mir versus Nog. This depends on whether Nog beats Randy. If he doesn't, then this fight is very likely. UFC 108.
Second choice: Mir versus Junior Dos Santos. The heavy-handed Brazilian's ground game will be tested. UFC 109.
Third choice: Mir versus Cheick Kongo. UFC 108.
If Georges St-Pierre wins
First choice: GSP versus Fitch. The rematch from UFC 87—I predict the UFC is trying to set this up by having them both fight on the same card at UFC 100. UFC 106.
Second choice: GSP versus Anderson Silva. The superfight could be GSP's next fight. UFC 107.
Third choice: GSP versus Mike Swick. If the superfight against Silva doesn't materialize, then this could be done at UFC 106 or UFC 107. But if GSP fights Anderson, expect this to be around UFC 111.
Dark Horses: GSP versus Martin Kampman. UFC 106. GSP versus Paulo Thiago UFC 106.
If GSP loses
First choice: GSP versus Mike Swick—more likely because UFC might not think Swick has done enough for a title shot. UFC 106.
Second choice: GSP versus Paulo Thiago. This depends on the result against Fitch at UFC 100. If Thiago loses, expect him to be easy prey for GSP, as the UFC hopes for a comeback. UFC 105
Third choice: GSP versus Anderson Silva. This is less likely if he doesnt have the belt, but because of fan pressure, the UFC might have to do this. UFC 108.
If Thiago Alves wins
First choice: Thiago Alves versus Jon Fitch. Fitch won their previous encounter, and Alves will look to avenge that loss. UFC 106.
Second choice: Thiago Alves versus Mike Swick. UFC 109.
Third choice: Thiago Alves versus Martin Kampman. UFC 109.
Dark Horses: Alves versus Anderson Silva. UFC 107. Alves versus BJ Penn. UFC 108.
If Alves loses
First choice: Alves versus Matt Serr. They both will be looking to bounce back from a loss. UFC 106.
Second choice: Alves versus Dan Hardy. UFC 105 is in the UK, so this would be the perfect fight to headline or co-headline the event. UFC 105.
Third choice: Alves versus Matt Hughes. Hughes will look to revenge his loss at the hands of Alves, but will ultimately fail. UFC 107.
If Dan Henderson wins
First choice: Dan Henderson versus Nate Marquart. With three possible No. 1 contenders, the UFC needs to cut that down. UFC 109.
Second choice: Dan Henderson versus Demian Maia. UFC 109.
Third choice: Dan Henderson versus Anderson Silva. This is a slight possibility, and I doubt the UFC will want Henderson against Silva again so soon. UFC 108.
Dark Horses: Dan Henderson versus Thales Leites. UFC 108. Dan Henderson versus Wilson Gouveia
If Henderson loses
First choice: Dan Henderson versus Wanderlei Silva. This would be their third fight against each other, and with the series tied at 1-1, it's a real possibility. UFC 107.
Second choice: Dan Henderson versus Yushin Okami. Okami is one of the multiple No. 1 contenders, and the UFC would like to get rid of his contendership, so a fight against Hendo makes sense. UFC 110.
Third choice: Dan Henderson versus Thales Leites. UFC 108.
If Michael Bisping wins
First choice: Michael Bisping versus Anderson Silva. Bisping has been guaranteed a title shot at UFC 105 if he beats Hendo. UFC 105.
Second choice: Michael Bisping versus Nate Marquart—to create a true No. 1 contender. UFC 109.
Third choice: Michael Bisping versus Demian Maia—to create a true No. 1 contender. UFC 109.
Dark Horses: Michael Bisping versus Victor Belfort. UFC 108.
If Bisping loses
First choice: Michael Bisping versus Yushin Okami. Bisping will fight at UFC 105, but who he fights depends on the result against Hendo. UFC 105.
Second choice: Michael Bisping versus Rousimar Palhares. The UFC will try to groom Bisping so he can contend again, and Palhares will be an easy will at UFC 105. UFC 105.
Third choice: Michael Bisping versus Wanderlei Silva. This is more of a personal favourite, but if you look at it, the sense is there. Wandy will want to fight someone on the decline, and Bisping will want to face a well-known fighter. UFC 105.
So, there you have it. If anyone has any information why these fights might not work, I would love to know.
By the way, that age before beauty thing came from Brock Lesnar when he called Mir a "pretty boy?!"