ByMatt Juul, writer at
MMA and Entertainment Writer
Matt Juul

If you thought a pesky thing like retirement talk would stop the legendary B.J. Penn from fighting, well think again.

Despite a brutal loss in his last outing to Yair Rodriguez, the former UFC champion is heading back to the Octagon this summer to face Russian-born, German journeyman Dennis Siver at . It'll be interesting to see how "The Prodigy" rebounds, and if he can get back into the win column for the first time in nearly seven years.

For now, a retrospective of Penn's decorated, 16-year UFC career, ranking the former two-division champions opponents in the Octagon.

17. Joey Gilbert

While he may not be a household name, Joey Gilbert will go down in history as the first man to ever face Penn in a professional MMA fight.

The former boxer-turned-lawyer welcomed Penn to the Octagon during an undercard match at UFC 31 and quickly learned why they called him "The Prodigy." Penn pretty much dominated the bout, spending most of the first round in top control before finishing Gilbert with a last second TKO.

16. Paul Creighton

A black belt whiz under Renzo Gracie, things were looking up for Paul Creighton when he landed a spot in the UFC. Then he faced Penn.

While it wasn't exactly the grappling tete-a-tete fans were expecting, their lightweight scrap at UFC 37 was an entertaining affair. After a back-and-forth first round, Penn turned up the heat in the second frame, eventually finishing Creighton via TKO from mount. Creighton would hang up his gloves for good following the defeat.

15. Yair Rodríguez

Photo by Mark J. Rebilas / USA Today Sports
Photo by Mark J. Rebilas / USA Today Sports

A sign of the times, proved why MMA is a young person's sport with his utter destruction of Penn at .

: Latin America winner got a chance to showcase his skills in the headlining matchup, easily out-maneuvering the much older Penn at every turn. Rodriguez would go on to win a Performance of the Night bonus with his second round TKO of "The Prodigy."

14. Joe Stevenson

UFC 80 turned into quite the bloodbath courtesy of Penn and , who were vying for the vacant lightweight title at the time.

Clearly motivated, Penn put on a master class against Joe "Daddy," pummeling his face with vicious ground-and-pound before securing a tight, rear naked choke just over four minutes into the second frame. The image of Stevenson's bloody face as he's being choked out by Penn will forever be seared into our brains.

13. Din Thomas

Retired UFC fighter Din Thomas had the pleasure of facing Penn in his first UFC fight, and no, it didn't go well for "Dinyero."

The Hawaiian phenom only needed one round to put Thomas away, finishing the fight via TKO less than three minutes into the opening frame at UFC 32. Luckily, Thomas' subsequent UFC appearances would turn out much better.

12. Caol Uno

One of the UFC's early Japanese stars, fan-favorite Caol Uno had a pair of memorable bouts with Penn.

The lightweight stars first squared off at UFC 34, where Penn demolished Uno with an 11 second KO. They faced off again in the finals of the lightweight championship tournament at UFC 41, however, the match was ruled a draw and neither fighter was awarded the belt.

Since Uno is technically not retired, perhaps he can finish his trilogy with Penn some day since it doesn't look like "The Prodigy" is quitting any time soon.

11. Diego Sanchez

Photo by Etzel Espinosa / USA Today Sports
Photo by Etzel Espinosa / USA Today Sports

Penn seemed virtually unbeatable during his lightweight title reign in the late 2000s, and his fight against was proof positive of that.

The TUF alum, as always, was fired up to face Penn, but quickly learned why challenging the Hawaiian star was a bad idea. Penn dominated the fight from bell to bell, eventually opening up a nasty cut over Sanchez's eye with a vicious head kick. Although it didn't knock Sanchez out, the wound was so crazy that the doctor had to call the fight midway through the final round, marking another bloody win for Penn.

10. Jon Fitch

Photo by UFC
Photo by UFC

Another battle of grappling masters, the welterweight scrap between Penn and Jon Fitch was an intriguing bout to headline UFC 127.

Unfortunately the fight wasn't as exciting as fans had hoped, with the match being scored a majority draw. While both fighters seemed willing running back the tape, neither the fans nor the UFC were interested in rebooking the bout.

9. Jens Pulver

Penn has been a part of several amazing rivalries, but his first feud came against former champ Jens Pulver.

The rivals squared off at UFC 35, where a younger Penn barely lost out on his first lightweight title bid, coming up just short in a decision. Penn and Pulver would face each other again following their stint as coaches on the fifth season of TUF. "The Prodigy" went on to win their bout at the finale thanks to a second round rear naked choke. These days, Penn and Pulver seem to be good buddies, so it's all water under the bridge.

8. Matt Serra

Long before their stints as welterweight champs, Penn and Matt Serra got a chance to face each other in the lightweight tournament semifinals at UFC 39.

It was a close fight between the veteran BJJ aces, but Serra ended up losing the match via unanimous decision. While it wasn't the most exciting fight to ever happen, the match was certainly a big challenge for Penn at the time.

7. Kenny Florian

Photo by UFC
Photo by UFC

Kenny Florian has fought for a title on multiple occasions, but his hardest championship bout occurred against "The Prodigy" at UFC 101.

An in-shape Penn came to fight that night, as he seemed to be firing on all cylinders against Florian. Constantly stuffing takedown attempts and owning the stand-up game, Penn was in control and never let "KenFlo" find his footing. Penn would go on to win the bout with a vicious rear naked choke in the fourth round to defend his belt.

6. Sean Sherk

In a fight that will forever be a part of Penn's highlight reel, the then lightweight champion showed Sean Sherk who's boss at UFC 84.

"The Prodigy" outclassed the former title holder, in particular, forcing him to eat a vicious flying knee at the end of the third round. The strike turned out to be the final blow, as Sherk wasn't able to answer the bell for the fourth frame, resulting in a TKO defeat for "The Muscle Shark."

5. Rory MacDonald

Photo by Marc DesRosiers / USA Today Sports
Photo by Marc DesRosiers / USA Today Sports

In a bout that Penn would probably like to forget, the former champ ended up on the wrong side of a beatdown during his matchup against Rory MacDonald at UFC on Fox in 2012.

Proving that the welterweight division has gotten a lot stronger since Penn's reign as the champ, MacDonald wiped the floor with "The Prodigy" before earning a unanimous decision victory over the legend. The fight would be Penn's last at 170 pounds, prior to his recent drop down to the featherweight division.

4. Nick Diaz

Penn was on the verge of another welterweight title shot before he stepped into the Octagon with fan-favorite Nick Diaz at UFC 137. Unfortunately, the Stockton Bad Boy spoiled his rise back to the top.

Although Penn started the fight off strong, he was unable to get his rhythm going, ultimately falling into Diaz's trap. The former champ outstruck the Hawaiian in the final two frames to take home the decision win and Penn's dream of another date with Georges St-Pierre.

3. Frankie Edgar

Photo Adam Hunger / USA Today Sports
Photo Adam Hunger / USA Today Sports

Penn's trilogy with in two different weight classes has been both exciting, and yet hard to stomach at the same time.

Edgar first shocked the world by beating Penn in back-to-back lightweight title fights at UFC 112 and UFC 118, which turned out to be entertaining decision wins for "The Answer." However, their final scrap at featherweight following their stint as TUF coaches in 2014 was just brutal, as Edgar easily defeated Penn, winning via a third round TKO. Hopefully "The Prodigy" doesn't try for a fourth go-around with the ex-champ.

2. Matt Hughes

As one of MMA's best trilogies, Penn's saga with Matt Hughes is the stuff of legends.

Penn made history when he took the welterweight belt from Hughes at UFC 46, defeating the champ with a slick first round rear naked choke. Their second scrap, at UFC 63, would also end in an exciting finish, this time with Hughes securing the victory with a third round TKO. However, Penn would go on to take the rubber match in this series, scoring a vicious 21-second KO over Hughes at UFC 123.

1. Georges St-Pierre

Photo by Joe Camporeale / USA Today Sports
Photo by Joe Camporeale / USA Today Sports

Without a doubt, former welterweight champion Georges St-Pierre is the best fighter who's ever faced Penn inside the Octagon. Their pair of bouts were must-see TV at the time, and are still great to watch if you happen to have Fight Pass.

The former champs first squared off in a welterweight title eliminator bout at UFC 58, where Penn came up just short in a split decision. After going on to win the lightweight crown, Penn would again try to challenge at UFC 94, but the results weren't all that great for "The Prodigy." After receiving a brutal beatdown, Penn's corner was forced to throw in the towel after four rounds of action.

Now that GSP's back with the UFC, maybe these former champs will finally get a chance to finish their trilogy. Stranger bookings have happened.

Don't forget to catch episode one of The Bas Rutten Experiment


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