Rematch Timeline | Max Holloway vs Charles Oliveira

Six months later, Holloway faced Anthony “Showtime” Pettis for the interim featherweight title in Toronto. Pettis, unfortunately, missed championship weight by three pounds, leaving only Holloway eligible to win the title.  

Oliveira: Submission Loss vs Anthony Pettis, Submission Loss vs Ricardo Lamas

Despite missing weight, Oliveira found himself in a marquee spot opposite former lightweight champion Anthony Pettis, who was moving down to featherweight for the first time. The fight was a back-and-forth affair, but Pettis wore on Oliveira before eventually submitting him via guillotine, just the second man to force the Brazilian to tap.

The third man to accomplish such a feat would, unfortunately, come in his next fight. Against Lamas in Mexico City, Oliveira tipped the scales 10 pounds over the limit, missing weight for the second time in three fights. Lamas would secure a guillotine choke midway through the second round, and Oliveira would move up to lightweight following the bout. 

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2017

Holloway: TKO Win vs José Aldo, TKO Win vs José Aldo

With the interim belt around his waist, Holloway turned his eyes to the great José Aldo. The unification bout came in the summer at UFC 212 in Aldo’s backyard of Rio de Janeiro, but the young Holloway was unfazed in hostile territory. Despite Aldo’s success early in the fight, Holloway remained steadfast and pounced when Aldo started to slow down, eventually earning the TKO finish in the third round and stunning the Brazilian crowd. 

Now the undisputed champion, Holloway was expected to fight former lightweight champion Frankie Edgar at UFC 218, but when Edgar withdrew due to injury, Holloway found The King of Rio in his sights again. The rematch played out similarly to the first, with Aldo finding some early success before Holloway gained momentum and bowled over Aldo to earn another third-round TKO. Beating the man considered the greatest featherweight of all-time twice in one year catapulted Holloway into that same discussion at just 26 years old.

Oliveira: Submission Win vs Will Brooks, TKO Loss vs Paul Felder

Moving up to lightweight proved fruitful right away for Oliveira. No longer draining himself to hit the 145-pound limit, Oliveira faced Will Brooks at UFC 210 and secured a rear-naked choke in the first round. For his work, he earned a Performance of the Night bonus. 

However, Oliveira would stumble at UFC 218. While Holloway defended his title against Aldo, Oliveira faced Paul Felder. Holding the American in his guard in the second round, he was hit with several elbows before the referee stopped the fight, his fourth loss in his last six fights. Although his future was perhaps cloudy heading into 2018, the loss would be his last one for the next four years.

2018

Holloway: TKO Win vs Brian Ortega

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If 2017 was a high-point for Holloway, 2018 was a year of difficulty. Once again booked to fight Edgar at UFC 222, the Hawaiian was forced to withdraw due to an injury. However, in April, Holloway jumped on the chance of a lifetime to replace Tony Ferguson and face lightweight champion Khabib Nurmagomedov at UFC 223. Looking to earn double-champ status, Holloway flew to New York City with six days to make weight, but the commission forced Holloway to stop on the eve of the fight, scrapping the matchup. 

In the midst of the shuffle, Edgar fought Brian “T-City” Ortega and suffered a knockout loss for the first time in his career. This launched Ortega into the No. 1 contender spot, and so Holloway was booked to face the undefeated Los Angeles-native in the summer at UFC 226. Three days before the fight, though, Holloway was pulled from the bout due to “concussion-like symptoms,” the third time that year Holloway was forced to pull out of a matchup. 

Question marks buzzed around “Blessed” heading into the rebooked matchup with Ortega at UFC 231 in Toronto. Ortega, then-undefeated, was viewed as having a great chance to unseat Holloway, but instead, Holloway turned in his finest performance to date. From the start, Holloway was several steps ahead on the feet and denied any chance for Ortega to get to his grappling. Having doled out punishment over the course of four rounds, Holloway scored a TKO win when the Octagonside doctor deemed Ortega unable to continue. 

In the fight, Holloway landed 290 significant strikes, a record for the most in a single fight. He secured his 15th win as a featherweight, the most in UFC history. Emphatically, Holloway asked: “Is there anyone else?”

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Oliveira: Submission Win vs Clay Guida, Submission Win vs Christos Giagos, Submission Win vs Jim Miller

In 2018, Oliveira made the move to Chute Boxe in São Paulo to round out his game and sharpen his Muay Thai. He has stayed with the team since, and it was this same year that he started to find some consistency. 

First came a matchup with Clay Guida, who replaced an injured Bobby Green. A little more than two minutes into the fight, Oliveira locked in a guillotine and scored his 10th submission victory, tying the record for most in UFC history. 

He would get to break the records at home in São Paulo when he faced Christos Giagos. Showing off his well-rounded game for most of the fight, he eventually found Giagos’ back, forced the tap, and cemented himself in the UFC record books. 

Three months later, Oliveira exacted some revenge on Jim Miller, who tapped Oliveira with a kneebar eight years prior. This time, Oliveira locked in an RNC, earning his third win and Performance Bonus of 2018.

2019

Holloway: UD Loss vs Dustin Poirier, UD Win vs Frankie Edgar, UD Loss vs Alexander Volkanovski

View Holloway's Athlete Profile

Holloway would go for double-champ status in earnest when he was tapped to face Dustin Poirier in an interim title bout at UFC 236 in Atlanta. The bout was a rematch of Holloway’s UFC debut, but “The Diamond” would outduel him once again in a memorable 5-round affair. The loss was Holloway’s first since 2013, but he remained the featherweight champion.

Returning to his 145-pound kingdom, Holloway finally faced Edgar in Edmonton and turned in a steady performance to defend the belt once again. However, Holloway’s trajectory would change in December when he faced Alexander Volkanovski for the first time. Although Holloway fought strongly, Volkanovski earned the judges’ nod on the scorecards, unseating Holloway from the throne.

Oliveira: Submission Win vs David Teymur, TKO Win vs Nik Lentz, KO Win vs Jared Gordon

After three wins in 2018, Oliveira kept the good times rolling in 2019. First came a matchup with David Teymur in Fortaleza. Oliveira looked sharp once again, allowing his striking to lead into his submission game. He rocked Teymur with an elbow before sneaking his arms around his neck with an anaconda choke, once again earning a Performance Bonus.

Oliveira followed that with a trilogy bout against Nik Lentz, and Oliveira scored his first UFC knockout in the second round. The improvements in his striking continued in his last fight of 2019 when he dropped Jared Gordon with his hands less than 90 seconds into their bout, earning yet another Performance Bonus. 

View Oliveira's Athlete Profile

2020

Holloway: SD Loss vs Alexander Volkanovski

Given Holloway’s dominant run through the featherweight division, it only made sense he would get an immediate chance at regaining the title. The COVID-19 pandemic threw a wrench in the timeline, but eventually, the rematch took place at UFC 251 on Fight Island. Holloway started strong, scoring knockdowns and rocking Volkanovski on several occasions in the first couple of rounds. However, Volkanovski made adjustments to take the final three rounds on the scorecards, defending the belt via split decision. The result remains one of the most debated of the decade, but Holloway would have to figure out a way to get another shot at the belt.

Oliveira: Submission Win vs Kevin Lee, UD Win vs Tony Ferguson

Oliveira was building a sneaky case for himself as a legitimate contender at the start of the decade, and when he headlined UFC’s last event before the COVID-19 shutdown, he emphatically announced himself in full as he submitted Kevin Lee in the third round of their bout.  He followed that performance with a dismantling of Tony Ferguson nine months later, including a brutal armbar attempt, solidifying himself in the title picture. 

2021

Holloway: UD Win vs Calvin Kattar, UD Win vs Yair Rodriguez

While some questioned Holloway’s future, “Blessed” simply got better. Headlining UFC’s first show on ABC, Holloway put on a record-breaking performance against Calvin Kattar. Although Kattar never went down, Holloway set single-fight records for total strikes landed and attempted, significant strikes landed and attempted, and most strikes landed in a single round among many others. He also, famously, declared himself the best boxer in the UFC on his way to a unanimous decision with scorecards of 50-43, 50-42 and 50-42. 

Not resting on his laurels, Holloway eventually faced Rodriguez in November and won a grueling fight via unanimous decision, earning Fight of the Night honors. Rodriguez gave Holloway all he could handle, but the former champion showed off his wrestling skills to gain control of the last half of the bout. 

Oliveira: TKO Win vs Michael Chandler, Submission Win vs Dustin Poirier

Undoubtedly the best lightweight fighting, Oliveira went into his second title defense with all the momentum in the world. The only thing that could beat him, it seemed, was a wonky and controversial scale in Phoenix. Despite believing he was on weight, Oliveira tipped the scales a half-pound over the championship limit, and he was stripped of the title upon entering the Octagon for his fight with Justin Gaethje. However, he turned in another vintage performance, recovering from an early knockdown to drop Gaethje before submitting him in the first round. He may not have had the belt, but in most everyone’s eyes, he was the champion. 

Looking to stamp that claim, Oliveira faced Islam Makhachev in Abu Dhabi, hoping to regain the title and continue his legendary run. However, Makhachev was sharp, controlling Oliveira early before knocking him down and submitting him in the second to start his own reign. 

2023

Holloway: UD Win vs Arnold Allen, KO Win vs The Korean Zombie

Although other fighters may have lost motivation following a third loss to the champion, Holloway simply went about his business. First came a main event against the rising Arnold Allen, but Holloway came out with a methodical and measured approach, outclassing the Englishman over five rounds. He followed that with a long-awaited bout against The Korean Zombie in his farewell fight. Fighting in the wake of the wildfires that rocked Maui, Holloway delivered another memorable moment, knocking the Korean title challenger out in the third round. 

Oliveira: TKO Win vs Beneil Dariush

Looking to get another shot at Makhachev, Oliveira signed up to fight the streaking Beneil Dariush, eventually facing the American in Vancouver. Oliveira steamrolled Dariush, loudly declaring himself, at-worst, the second-best lightweight in the world and leaving many wanting to see a rematch between the champion and him. The rematch was booked for UFC 294, but a cut suffered days before the fight forced Oliveira out of the bout, and he wasn’t able to challenge for the title before the year’s end.

2024

Holloway: KO Win vs Justin Gaethje, KO Loss vs Ilia Topuria

Heading into 2024, Volkanovski was still the dominant featherweight champion, so Holloway took a chance and challenged Justin Gaethje for the BMF title at UFC 300. He couldn’t have predicted Ilia Topuria would knock Volkanovski out two months earlier, but that was business for later in the year. Against Gaethje, Holloway turned in an all-around dominant performance, stunning Gaethje several times before, famously, pointing down to the center of the Octagon like he did years ago against Lamas and inviting a slugfest. With a second to go, Holloway connected with a right hand that reverberated across the MMA world, a knockout that will live on for all time. 

He parlayed that moment into a shot against Topuria, looking to finally regain his title five years after losing it to Volkanovski. Unfortunately, he instead suffered the first knockout loss of his career, and Holloway would announce his departure from the featherweight division for good.