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| February 2025 | Confirmed via Twitter that he will permanently stay in the Lightweight weight class. |
| October 26 2024 | Challenged Ilia Topuria for the UFC Featherweight Championship at UFC 308, suffering his first career knockout loss in the third round. |
| April 13 2024 | Defeated Justin Gaethje by knockout in the last second of round five at UFC 300, winning the symbolic 'BMF' belt. Earned $600,000 in bonuses ($300,000 Performance of the Night and $300,000 Fight of the Night), and tied the record for the latest knockout win in UFC history. |
| 2023 | Served as a guest judge on Drag Race Philippines in the episode 'The Main Event' |
| 2023 | Collaborated with Wanderlust Creamery to create an ice cream flavor 'Da Fruity Salad' for Filipino American History Month. |
| 2023 | Became the UFC 'BMF' Champion, further solidifying his status as a top fighter in the organization. |
| August 26 2023 | Knocked out Jung Chan-sung at the beginning of the third round at UFC Fight Night 225, earning a Fight of the Night award for an impressive performance. |
| April 15 2023 | Defeated Arnold Allen by unanimous decision at UFC on ESPN 44, demonstrating his continued skill in mixed martial arts. |
| February 2023 | Harper published Rock's memoir titled 'You're That Bitch'. |
| 2022 | MTV's 'Following: Bretman Rock' was nominated for Outstanding Reality Program at the GLAAD Media Award. |
| 2022 | Voiced the character 'Makeup Boy' in The Proud Family: Louder and Prouder, appearing in episodes 'Bad Influence(r)' and 'BeBe' |
| 2022 | Bretman Rock was nominated for Best Instagram at the WOWIE Awards. |
| July 2 2022 | Fought Alexander Volkanovski in a trilogy bout at UFC 276, losing via unanimous decision in the UFC Featherweight Championship fight. |
| April 16 2022 | Max Holloway married Alessa Quizon. |
| March 5 2022 | Holloway was originally scheduled to fight Alexander Volkanovski for the UFC Featherweight Championship at UFC 272, but was forced to pull out of the event due to an injury. |
| 2021 | Bretman Rock's show '30 Days With: Bretman Rock' won Show of the Year and Unscripted Series of the Year at the Streamy Awards. |
| 2021 | Won the People's Choice award for 'Beauty Influencer'. |
| November 13 2021 | Holloway fought Yair Rodríguez at UFC Fight Night 197, winning via unanimous decision. Both fighters earned the Fight of the Night award. |
| October 2021 | Became the first openly gay man to appear on the cover of Playboy magazine. |
| August 2021 | Made a cameo appearance in Sub Urban and Bella Poarch's music video for 'INFERNO'. |
| June 2021 | Nominated for and won MTV Movie and TV Award in the Breakthrough Social Star category. |
| June 17 2021 | Holloway was reported to have pulled out of a scheduled fight with Yair Rodríguez due to injury. |
| June 15 2021 | YouTube Originals announced Rock as the subject of their '30 Days With' documentary series. |
| May 14 2021 | Made a cameo in Bella Poarch's music video for her debut single 'Build a Bitch'. |
| February 9 2021 | First episode of 'MTV Following: Bretman Rock' premiered on MTV's YouTube channel. |
| January 28 2021 | MTV announced Rock would star in his own reality TV show 'MTV Following: Bretman Rock'. |
| January 16 2021 | Holloway fought Calvin Kattar at UFC on ABC 1, dominating all 5 rounds and winning by unanimous decision. He set multiple UFC single-fight records for strikes landed and attempted, including records for total strikes, significant strikes, strike differential, distance strikes, and head and body strikes. Both fighters earned Fight of the Night award. |
| 2020 | Became a finalist in comedy video at the Shorty Awards, expanding his recognition beyond beauty content. |
| 2020 | Featured on Variety's 2020 Power of Young Hollywood list, recognizing his influence in entertainment and media. |
| 2020 | Holloway began dating Hawaiian pro surfer Alessa Quizon. |
| November 2020 | Launched eyewear collection in collaboration with Dime Optics, releasing six sunglass frames. |
| July 12 2020 | Max Holloway competed against Alexander Volkanovski in a UFC Featherweight Championship rematch at UFC 251, losing via controversial split decision. 18 out of 27 media scores favored Holloway, and notable figures like Dana White, John McCarthy, and other mixed martial artists disputed the decision. |
| May 9 2020 | Appeared as a guest star on James Charles' YouTube Originals series 'Instant Influencer'. |
| April 2020 | Rock publicly requested on social media that fans not visit his home uninvited, particularly during the COVID-19 pandemic, after two people approached his residence and left a note on his car. |
| February 2020 | Launched makeup collection in collaboration with wet n wild cosmetics, conducting a press tour in Los Angeles. |
| 2019 | Earns the UFC 'BMF' Champion title, further solidifying his status as a prominent figure in mixed martial arts. |
| 2019 | Won the Beauty Influencer award at the 45th People's Choice Awards, solidifying his status in the beauty and social media industry. |
| December 2019 | MTV announced Rock would star in the next season of YouTube show No Filter. |
| December 14 2019 | Lost UFC Featherweight Championship to Alexander Volkanovski via unanimous decision at UFC 245, ending his featherweight title reign. |
| December 4 2019 |
Pearl Harbor
A US Navy sailor killed two civilian workers and wounded another at the Pearl Harbor Naval Shipyard before shooting himself.
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| November 2019 | Bretman Rock's father passed away after being in a coma. |
| September 2019 | Attended his first New York Fashion Week, collaborating with stylist Andrew Gelwicks. |
| September 2019 | Bretman Rock shared in an Elle interview that he was in his first relationship. |
| July 2019 | Played 'The Playboy' in the fourth season of YouTube Premium web series Escape the Night. |
| July 27 2019 | Defended UFC Featherweight Championship against Frankie Edgar at UFC 240, winning by unanimous decision and successfully defending his title for the third time. |
| June 2019 | Featured on the Pride Month cover of Gay Times magazine. |
| April 13 2019 | Max Holloway fights Dustin Poirier in a rematch at UFC 236 in Atlanta, Georgia |
| 2018 | Included in Forbes '30 Under 30 Asia – Media, Marketing, & Advertising' list. |
| December 8 2018 | Defended UFC Featherweight Championship against Brian Ortega at UFC 231 in Toronto, winning via TKO in the fourth round. Broke records for most significant strikes in a fight (290) and most victories in UFC featherweight history (15). |
| July 4 2018 | Withdrawn from UFC 226 title defense against Brian Ortega due to 'concussion like symptoms'. |
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This contents of the box above is based on material from the Wikipedia articles Pearl Harbor, Max Holloway & Bretman Rock, which are released under the Creative Commons Attribution-ShareAlike 4.0 International License.