The UFC as an organization has given us some unforgettable moments since its establishment in 1993. It has achieved different milestones and became the most renowned mixed martial arts organization in the world. It has brought the sport of MMA to mainstream audiences.

There have been so many moments to cherish for the fans, some tense, some absolutely feel-good, and delightful. However, there have been other moments that were absolutely heart wrenching for fans all around the world. For some, it was seeing their favorite fighter lose. For others, it was them retiring. These moments have been etched forever in UFC history and the memories of MMA fans.

BJ Penn’s UFC Retirement

The “Prodigy” was widely regarded as one of the best mixed martial artists in the sport. He is ranked as the best lightweight ever by many because of his three title defenses in the UFC. Penn, however, faced a major downfall in his career after a certain point losing thrice in a row against the likes of Nick Diaz, Rory MacDonald, and Frankie Edgar.

When asked in the post-fight press conference about his decision to retire, Penn said:

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“Yes, of course, this is the end, I’m thinking to myself why did you step back in the octagon after the beating that Rory MacDonald gave you? And the reason is because I really needed to find out.

“If I didn’t make this night, make this night happen, I would’ve always wondered and went back and forth and begged Dana to let me get back in. And I guess I just needed some closure“.

He broke down while bidding his farewell to the organization. This made the fans teary-eyed. Seeing one of the greatest and most beloved fighters calling it a day will make anyone cry.

Anderson Silva’s First UFC Loss

Whenever there is talk about the GOAT of mixed martial arts, Anderson “The Spider” Silva is a name that is always in the conversation. Being one of the most dynamic and skilled strikers in the history of MMA, he made high caliber champions look like amateurs having no business in the cage with him.

Popular for his creative, unorthodox striking and his ability to have fun in the cage at the expense of his opponent, Silva quickly made a name for himself in the division with his destruction of veteran fighter Chris Leben within the first minute of the fight.

Silva followed this by brutally kneeing then middleweight champ Rich “Ace” Franklin the entire fight to become the undisputed middleweight champion. He then defended his title a record 14 times, thus winning all his 16 fights in a row. And was undefeated in the UFC until he squared up against the young contender Chris Weidman.

The odds were in favor of Silva as everyone thought he would get the job done in style, like always. However, not taking Weidman as much of a threat, Silva started goofing around in the cage and became too careless, dropping his hands and letting Weidman punch him in the face. Everyone seemed to enjoy this until Weidman landed a clean left hook on Silva’s chin, knocking him out cold, and shocking the entire world.

Many fans and critics, however, termed it as a “fluke” and said Silva only lost because he didn’t take the fight seriously. A rematch was fixed between the two where Silva was expected to redeem himself and take back his title.

Fans were eager to see how a motivated “Spider” would exact his revenge. However, the fight ended in disappointment once again, much to the chagrin of Silva and his ardent fans who had flocked up to see him put on a show. Weidman checked one of Silva’s leg kicks, snapping his leg in half.

The fans present in the arena that night and all around the world grimaced at the sight of Silva’s gruesome injury. Everyone knew that this was the end of an era. This moment remains one of the saddest and most depressing moments in UFC history.

Randy Couture Calling It Quits

Randy “The Natural” Couture was one of the biggest and most beloved names in all of UFC. Having won the UFC heavyweight championship thrice, the light heavyweight championship twice, the Interim light heavyweight championship once, and being the first fighter to win UFC championships in two different weight divisions, made him a fan favorite.

However, age takes its toll on everyone. Couture fought Lyoto Machida, who had recently lost his UFC light heavyweight championship and was looking to get back in the win column. The fight ended with Machida hitting Couture with a devastating crane kick, which ended up knocking Couture out cold.

The fans already knew what was next, so it did not come as a surprise when Couture announced his retirement from the sport of MMA as he couldn’t compete with the best anymore. Though expected, it was a tear-jerker for everyone to see the hero, who inspired so many people, leave once and for all.

Daniel Cormier’s Two Devastating Losses

One of the greatest and the best pound-for-pound fighters ever, Daniel “DC” Cormier recently announced his retirement from the sport of MMA after his trilogy fight with heavyweight champion Stipe Miocic. His career was nothing short of an incredible story of an underdog who overcame his physical disadvantages against much bigger opponents through pure grit and determination. He made a name for himself in Strikeforce, which was eventually absorbed by the UFC.

In the UFC, he beat contenders one after the other, using his Olympic wrestling background and a much-improved stand-up game. He remained undefeated till he met the pound-for-pound king of the organization, Jon “Bones” Jones. In a highly anticipated match-up between the two undefeated fighters (with Jones’ only loss coming via disqualification), Jones defeated DC and left him heartbroken.

The rematch scheduled for UFC 200 was scrapped after Jon Jones tested positive for banned substances. As a result, DC would face middleweight Anderson Silva, who made his debut in the light heavyweight division. The former won by unanimous decision.

He fought Jones once again at UFC 214. The fight, however, didn’t go as planned for DC who was knocked out brutally by a head kick followed by a barrage of punches on the ground by Jones. Seeing him cry in the post-fight interview was sad to watch.

DC, however, had his glory moments next year, recapturing the vacant light heavyweight title. This happened after the UFC stripped Jones once again for testing positive for a second time. He then knocked out Stipe Miocic in the very first round to win the heavyweight gold. One year later, he tried to defend his title for the second time against Stipe in a rematch. Unfortunately, he lost via a fourth-round TKO.

This set the stage for the ultimate trilogy bout between two of the best heavyweights not just in the UFC but of all time. Cormier announced that this will be his retirement fight as he was looking to cement his legacy as the greatest heavyweight of all time. The fans wanted to see DC ride off into the sunset after this fight.

The fight was nothing short of spectacular, however, Cormier suffered a brutal eye injury after a hard eye-poke in the third round of the fight. This affected his vision to a great extent and may have cost him the fight. Seeing such a great fighter and a role model end his career as a runner-up once again was deeply saddening.

Chuck Liddell’s Retirement From UFC

Chuck “The Iceman” Liddell was one of the biggest stars of the 2000s, bringing the sport of MMA and the UFC itself to mainstream popularity. He remains one of the most well-known figures in the world of combat sports. His relentless style of fighting and always going for the knockout earned him popularity amongst UFC fans.

Liddell relied on his speed, punching power, and his ability to absorb punishment to overwhelm his opponents. He won the UFC light heavyweight championship by knocking out Randy Couture and defended the title 4 times. He eventually lost it to Quinton “Rampage” Jackson via TKO.

Eventually, Liddell took too much damage inside the octagon. He lost 4 of his last 5 fights in the UFC. His last loss came through a brutal knockout at the hands of Rich “Ace” Franklin, which was painful to watch for everyone. At the post-fight press conference, Dana White announced that this was Liddell’s last fight in the UFC.

Following this, Liddell choked up while giving an emotional farewell speech to the UFC, the media, and the fans around the world. This was one of the saddest and most heart-wrenching moments for fans all around the world, who were aware of how badly they will miss him.