Dan Henderson's 5 Potential UFC Middleweight Matchups

Mike Wellman@@mikewellman88Contributor IIIJune 25, 2014

Dan Henderson's 5 Potential UFC Middleweight Matchups

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    Add Dan Henderson’s name to the list of UFC light heavyweights looking for a career-resurgence by dropping to 185 pounds.

    MMAFighting.com reported that the former Pride two-division champion will be returning to middleweight for the first time since his 2010 fight against Jake Shields in Strikeforce.

    Hendo hopes to be back in the cage by the end of the year, and the middleweight division is as competitive as it’s ever been. With fighters like Tim Kennedy, Yoel Romero and Luke Rockhold currently jockeying for position in the top 10, there are a number of intriguing matchups for Henderson.

    Will we see him take on other legends and former champions in what will most likely be his last few fights?

    Perhaps Anderson Silva would be a good option if that will be in the case. If Henderson takes the alternative route and acts as a gatekeeper of sorts for the division’s younger, hungrier talent, then a fight with someone like Rockhold or even Costas Philippou would make sense.

    Here are the five best options for Henderson’s return to the middleweight division.

No. 5: Costas Philippou

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    USA TODAY Sports

    The danger that Philippou poses is in the power of his strikes, which is very similar to Henderson. Henderson has been reliant on the “H-Bomb” to get him out of bad spots over the last few years, and this fight would be guaranteed fireworks.

    Both guys have struggled against better grapplers and are usually far more willing to go toe-to-toe than their opponents are. Philippou absolutely starched Lorenz Larkin in his last fight and has been victorious in six of his nine UFC fights.

    This would be a great re-introduction to middleweight for Henderson and could definitely headline at UFC Fight Night card on Fox Sports 1.

No. 4: Yoel Romero

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    Henderson is a two-time Olympian in Greco-Roman wrestling, and Romero is an Olympic silver-medalist in freestyle wrestling.

    Throughout Henderson’s career, his wrestling credentials (along with his right hand) have been used as a selling point.

    Imagine the selling point being Hendo going up against someone who has actually medaled in the Olympics and also has one-punch knockout power.

    This is the go-to option if the goal for Henderson’s remaining fights is to put him in there against lesser-known competition to help elevate their profiles. Romero is 37, so the age disparity wouldn’t be huge in this fight.

    People have been wondering how slow the climb would be for Romero, who has one professional loss and seven of his eight wins have come by KO/TKO. He’s undefeated in the UFC and a fight with Henderson would be the perfect test to see if he can hang with the all-time greats.

    Throw this fight on a pay-per-view card and you have a fighter with name value going against a fighter that is certainly worthy of the exposure and the platform.

No. 3: Tim Kennedy

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    Kennedy proved in his most recent win against Michael Bisping that he can win and sustain his offense in a 25-minute fight.

    Prior to that, he scored a first-round knockout of Rafael Natal in front of a rabid crowd of U.S. troops at Fort Campbell. He out-grappled Roger Gracie and has shown thus far a well-rounded MMA game that continues to improve.

    Kennedy sits at No. 6 on UFC.com’s rankings and has a few UFC and Strikeforce main events under his belt. He's also undefeated inside the Octagon. The only thing his resume is missing is a victory over a legitimate UFC legend.

    Even though Henderson has won in only two of his last six fights, he is still ranked within the top 10 at light heavyweight. If the UFC plans to keep using him in marquee matchups, Kennedy is a better choice than Philippou or Romero.

    Both fighters are fan favorites among the American fanbase. It would be interesting to see how the crowd would react to an Army Ranger taking on a two-time U.S. Olympian.

No. 2: Luke Rockhold

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    Rockhold and Henderson have something in common: Both were victims to the TRT-fueled tear that Vitor Belfort went on while fighting only in Brazil throughout 2013.

    It was Rockhold’s Octagon debut, and he has rebounded with fantastic performances against Philippou and Tim Boetsch.

    Rockhold is a top-five middleweight. He may pose the toughest test for Henderson due to his diverse arsenal of strikes and his ever-improving ground game. This fight could easily headline a UFC on Fox event or co-main event a pay-per-view show.

    A win over a legend like Henderson would greatly improve Rockhold’s popularity and firmly establish him as a main event, championship-level fighter. If the UFC wants to build Rockhold into a top draw, he needs a big win against a very well-known fighter.

    Though Rockhold would most likely be a favorite on the betting lines, a thunderous KO by Henderson would fend off talk of retirement and add a great name to his already unreal resume.

No. 1: Anderson Silva

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    USA TODAY Sports

    Anderson Silva is currently gearing up to get back into training full-time after his gruesome leg injury suffered in his rematch with Chris Weidman at UFC 168 back in December. He most likely won’t be ready to return to the cage until the beginning of 2015.

    Who knows how Silva is going to look upon returning? He will be nearing 40 years of age himself when he comes back, so age would hardly be a factor in this matchup.

    Silva defeated Henderson to merge the Pride welterweight and UFC middleweight titles at UFC 82 in 2008. A rematch with Henderson would be a great comeback fight for the former champion.

    It’s a fight that makes sense for both men and isn’t entirely unwinnable for Henderson.

    This fight could easily be used as a co-headliner underneath a bantamweight or flyweight title fight on pay-per-view and would draw some eyeballs.

    There are a lot of options for Henderson in his trip back down to middleweight, and Anderson Silva is the best one.