TITO ORTIZ vs. WANDERLEI SILVA

(The abridged version of the fight, which Ortiz won by unanimous decision.)

When it happened: 4/14/00, at UFC 25
When it should have happened: Spring 2003
Why: Ortiz vs. Silva was an entertaining scrap between two young contenders for the UFC’s vacant "middleweight" belt. If they met three years later, it would have been a superfight. By the end of 2002, Ortiz had defended his title five times — he’d lose it in September 2003 to Randy Couture — while Silva was PRIDE’s middleweight ruler, owning a 12-0-1 record in the promotion and two successful title defenses. With Ortiz at the end of his reign and Wandy near the middle of his, it would have been an ideal moment to establish bragging rights for one of MMA’s two leading organizations.
Prediction: Depends on where the fight was held. If Ortiz had home-field advantage, he’d probably still be able to grind out a decision win. In Japan, it would be Wanderlei via soccer-kick death.

DIEGO SANCHEZ vs. KENNY FLORIAN

(Click the image to go to the video. Sanchez def. Florian via TKO, 2:49 of round 1.)

When it happened: 4/9/05, at the Ultimate Fighter 1 Finale
When it should have happened: Sometime next year.
Why: Kenny Florian had enough talent and heart to make it to the finals of TUF 1 as a 185-pounder, but it was only a matter of time before he was squashed by another talented fighter who was more experienced and better suited to the weight; Diego Sanchez just happened to be that dude. This year, there was talk — hope, even — that Florian could upset BJ Penn at UFC 101, then have a high-stakes rematch against his old nemesis, who had followed him down to lightweight after an impressive run at 170. Unfortunately, Florian succumbed to Penn’s trademark mata leon, and Sanchez was booked to challenge Penn for the title in December. Still, as long as Florian keeps winning, he’ll claw his way back to the Nightmare — and this time, they’ll face each other as two of the best lightweights in the world.
Prediction: Sanchez outstrikes Florian to a decision in a far more competitive match than their first meeting.

ANDERSON SILVA vs. YUSHIN OKAMI

(Okami def. Silva via disqualification [illegal upkick], 2:33 of round 1)

When it happened: 1/20/06, at Rumble on the Rock 8
When it should have happened: 4/18/09, at UFC 97
Why: Mostly so people can stop bitching about how Yushin Okami has never gotten a UFC title shot. Of course, there’s some validity to that complaint: Okami may have a reputation as a boring fighter, but it’s hard to deny his talent or his status as a top middleweight contender, and when we watched the unworthy Thales Leites butt-flop his way through one of the worst title fights in UFC history at UFC 97, we couldn’t help but wonder if Thunder Okami would have given the Spider a better fight. Judging from their previous match at Rumble on the Rock’s 175-pound tournament in 2006, it would have at least been a more entertaining one. And at this point, we think Silva would know better than to knock out his opponent with an illegal upkick.
Prediction: Silva would have a second-round TKO victory on his record instead of a loss via DQ, and the world would be set right again.

KIMBO SLICE vs. ROY NELSON

(Nelson def. Slice via TKO, round 2)

When it happened: Summer 2009, during the taping of The Ultimate Fighter: Heavyweights.
When it should have happened: Summer 2012
Why: Look, we’re all for throwing YouTube brawlers into deep water to see if they really deserve to be considered mixed martial artists, but Roy Nelson was waaaaaaay out of Kimbo’s league on TUF 10. It just wasn’t a fair fight, and we couldn’t help but feel that it was a waste of Slice’s first Octagon appearance. (If only there was a way to guarantee that Kimbo could get through the show fighting the Abe Wagners and Wes Shiverses of the world.) Three more years spent drilling takedown defense and jiu-jitsu — and building up cage experience against less worthy opponents — would have served Kimbo well in a fight against someone of Big Country’s caliber.
Prediction: Nelson via submission (armbar), round 3. Rather than go out like a bitch, Kimbo would let his arm snap. Nelson and Slice would each be awarded $250,000 Fight of the Night bonuses by UFC president Shane McMahon.

ALISTAIR OVEREEM vs. CHUCK LIDDELL

(Liddell def. Overeem via KO, 3:09 of round 1)

When it happened: 9/10/03, at PRIDE Total Elimination 2003
When it should have happened: 12/31/09 at Dynamite!! 2009
Why: The way Bas Boon tells it, Alistair Overeem’s inconsistent performance as a 205-pounder back in PRIDE was due to excessive weight-cutting. So really, his loss to Chuck Liddell during PRIDE’s 2003 middleweight tournament shouldn’t even count. Now that Overeem is fighting at his natural weight — and we stress the word natural — it seems like a logical time to take on Chuck in an open-weight freak-show bout in Japan on New Year’s Eve, especially since Dana White won’t let Liddell fight in the UFC anymore. Chuck is probably delusional enough to think that he’d still have a good chance against Overeem, and as long as Alistair doesn’t have to face a top-ten heavyweight, he’d be happy to pick up the paycheck.  
Prediction: Overeem via brutal head-kick knockout, followed by gruesome synthol leakage.

Honorable mentions:
- BJ Penn vs. Takanori Gomi
- Lyoto Machida vs. Rich Franklin
- Jon Fitch vs. Thiago Alves
- Mike Brown vs. Masakazu Imanari