When these two fighters first faced off, "Showtime" emphatically decisioned "Smooth" to take the WEC belt with his famous, fifth round off-the-cage kick in the promotion's final show at WEC 53.
Since then, the careers of both men have taken some twists and turns, as Henderson has risen to become the defending UFC lightweight champ while Pettis has been on a roller coaster ride en route to his current shot at the belt.
Let's take a deeper look into how two of MMA's best 155ers stack up against each other in this rematch with this head-to-toe breakdown.
There are few fighters in MMA who are as creative with their striking as Pettis is.
While these moves may look super flashy, they are also pretty dangerous as Pettis has won back-to-back Knockout of the Night honors with his powerful head kicks.
The reigning UFC champ is also pretty slick with his striking, oftening throwing heavy kicks of his own, including less conventional strikes such as the downward heel kick. Henderson also has solid skills with his hands as well and has edged out talented boxers, from Frankie Edgar to Nate Diaz.
Pettis has proven to be more of a finisher in the stand up department, however, while "Smooth" has really only been effective in using his striking in conjunction with his wrestling to eek out points and decisions.
Both guys were pretty much evenly matched in their first meeting—save for the last minute of round five—but because of "Showtime's" recent dominant performances, he gets the edge in this department.
One area where the champ has a bit of a significant advantage in is in the wrestling department.
Since coming to the UFC, Henderson has been able to dominant grappling aces such as Jim Miller and Clay Guida as well as win head to head matchups on the mats against former champs like Frankie Edgar and Gilbert Melendez.
While wrestling standouts like Edgar have given "Smooth" some trouble in the Octagon, he's been able to stay ahead on the cards by keeping his cool in bad spots while utilizing slick transitions and powerful takedowns to impress the judges.
Pettis has improved his wrestling over the years, training with Bellator welterweight champ Ben Askren, but his takedown defense still needs some work—unless he keeps knocking people out in the first round.
The Milwaukee native likes to work off his back as well and is pretty dangerous in his guard, but that doesn't always do it for the judges.
"Showtime" seemed to be able to hang with Henderson on the mats in their first meeting, but the reigning UFC champ is clearly the more technical wrestler out of the too.
Image via espn.com
Henderson may have the edge in wrestling, but when it comes to jiu-jitsu, these two are pretty evenly matched.
The champ, who has eight career wins via submission, was recently awarded his black belt in BJJ and has been a frequent competitor on the grappling circuit lately.
Known for his ability to survive even the deepest chokes and subs, Henderson has improved his defense even more since his days in the WEC.
The champ has a fantastic guillotine choke which is a dangerous weapon when paired with his fantastic wrestling base.
While Pettis doesn't sport a black belt in the art, he's proven to be an excellent BJJ practitioner, owning six career wins via submission.
"Showtime" loves to use the triangle choke and has a very active guard which has given even wrestlers like Clay Guida trouble.
I'm not sure how long these two will tussle on the mats, but you can be sure it will be a very exciting and evenly matched exchange of submission attempts.
Having gone the distance in each of his last eight fights, there's no questioning Henderson's cardio in the cage.
The reigning lightweight king has gone to a decision in every single one of his UFC fights, going the full five rounds in his last four championship bouts.
In addition to his top level cardio, Henderson has also proven to be one of the stronger guys in the division, out muscling most of the 155ers since he cuts from such a higher weight than the majority of the fighters in the division.
Pettis is by no means completely out matched in this department as he also possesses world class athleticism and is constantly training in the gym. But the champ will have a small edge.
The last WEC lightweight champ is slightly smaller in size than the hulking Henderson and has only gone to a decision five times in his career.
While "Showtime" can clearly go five rounds, as his first meeting with the champ can attest to, it will be interesting to see if he can keep the pace this time around.
Henderson: While his recent performances have been close decisions, the reigning UFC champ has been on a tear since joining the UFC.
The "Showtime Kick" clearly pushed and motivated Henderson, but can he keep the streak going now that he has a chance to avenge his sole loss during his Zuffa tenure?
Pettis is also a very different fighter than Henderson's recent opponents, so it will be interesting to see if he changes up his gameplan at all.
Pettis: For the last WEC lightweight champion, finally getting a crack at a UFC title will be a joyous moment for Pettis.
While he's been longing to face someone for a shot at UFC gold, taking on Henderson again, in Milwaukee no less, is a dream come true.
The pressure will be on for "Showtime," although I'm sure he'll handle it just fine.
I expect this fight to pretty much go the same way the first fight did.
It's going to be close, go the distance and be insanely exciting. The only difference this time around will be the outcome.
Henderson has improved by leaps and bounds since his days in the WEC and has rolled over the best of the best in the lightweight division since joining the UFC.
Pettis has also improved since their first meeting, but "Smooth's" powerful wrestling and more tactical gameplan may be what earns him the nod.
This fight is anyone's to win, but I see the champ retaining his title.
Prediction: Henderson via split decision