Introduction (2008–2011)

Championship was announced on October 13, 2008 via IWA's website^[2] but it was not until February 14, 2009 at "Noche de Campeones" in Bayamón, Puerto Rico that it was determined a champion.^[3] The Inaugural champion was GQ The Ravishing (Richard Rondón), he won a 15 Man Tornado Rumble Match by last eliminating Cruzz.

Unified Puerto Rico Championship (2011–2012)

The championship would be unified with the IWA Puerto Rico Heavyweight Championship on February 26, 2011. On that match Xix Xavant defeated Romeo to unify the titles.^[4]

The Caribbean Heavyweight Championship was brought back in 2012 for the IWA/EWO Clash of the Titans show, a co-promoted one with another Puerto Rican Wrestling promotion called EWO. On this show, the winner of the match was Cyrus who won a 8 Man "Lucha X" Match where he defeated 8 participants who were.

Major League Wrestling (2019–2022)

Reintroduced as a regional third-party title (simply known as the “Caribbean Heavyweight Championship”) at Major League Wrestling in 2019, with Savio Vega billed as the current champion, the accolade was used to promote his arrival as part of Salina de la Renta’s Promociones Dorado (which he later left by ripping his contract).^[5] The incumbent was immediately given an opportunity for the MLW National Openweight Championship against Alexander Hammerstone of The Dynasty in what was branded an opportunity to become a double titlist, but ultimately saw the latter retain by cheating.^[6] Vega was given epithets such as “legendary” and “ the king of the Caribbean”, being matched against young performers including the members of latter group and Promociones Dorado.^[7][8][9] On January 11, 2020, Richard Holliday took possession of the belt after winning a non-title match, self-proclaiming himself champion.^[10]

As the disputed Caribbean Heavyweight Champion, Holliday was portrayed as a cowardly villain, who refused to participate in a titular match at Puerto Rico but was willing to make “defenses” in places such as “St. Barth's or Bermuda”. One such instance had him purportedly retain by defeating one Edwin González at Necker Island, a private island that is part of the British Virgin Islands.^[11] An unofficial defense took place at the MLW vs. AAA Super Series at Tijuana (Mexico being part of the larger Caribbean Basin), where Holliday defeated Chessman to give his team an early advantage.^[12] The belt played a role in selling the high-end lifestyle of The Dynasty, being taken to places with nudist beaches, “gorgeous women [or] luxurious beachside cabanas“ and having stable members debate whether it was “the more relevant title” in MLW opposite the National Openweight Championship.^[13] The group would also visit the Caribbean for less scrupulous reasons, such as purchasing Vega's childhood house at Puerto Rico to turn it into a bed and breakfast.^[14]

The storyline evolved to feature Holliday demanding that the Caribbean Heavyweight Championship was incorporated, or “naturalized”, as an official title within MLW and have him recognized as incumbent.^[15] In response, “MLW's CEO [Court Bauer] met with Puerto Rican government officials about hosting a Caribbean Heavyweight Championship title fight“ to be held in 2021 (tentatively at the Roberto Clemente Stadium in Carolina).^[1][16] During the final week of October 2020, the association between IWA-PR and MLW became a formal alliance.^[17] In the lead up to the announcement, Holliday complained twice about not being officially listed in the champions gallery, calling it “misrepresentation” and expressing his desire to “win over” and become “the face” of the region, ultimately threatening to melt the belt.^[18] Vega responded by issuing a challenge to a Caribbean Strap Match (a type of contest that he made famous by defeating Stone Cold Steve Austin at In Your House 8: Beware of Dog) for the belt in Puerto Rico.^[19]

Following another challenge, the self-proclaimed champion accepted to compete in the specialty match.^[20] On January 27, 2021, Holliday defeated Vega due to the intervention of referee Tim Donaghy, beginning his first official reign after 382 days of illegal possession.^[21][22] He then migrated to a feud with Gino Medina, a former member of The Dynasty, retaining the belt in April. Since Fall 2020, several talents formally associated with Lucha Underground were brought into MLW as part of the Azteca Underground stable, including César Durán (previously known as Dario Cueto), who became the on-screen owner of IWA-PR.^[23] King Muertes (formerly Mil Muertes in Lucha Underground, and known in Puerto Rico as Ricky Banderas) defeated Holliday to win the title in a match with “Caribbean Rules” at Battle Riot III.^[23]

At Fightland, he won his first defense by besting former MLW World Heavyweight Champion Tom Lawlor in a casket match. Muertes retained over Holliday in a rematch. On March 31, 2022, he defended the title in a four-way match against eventual winner Octagón Jr., El Dragón and El Hijo de L.A. Park. In his first defense, he retained over Matt Cross at Rise of the Renegades.

Return to IWA-PR (2022–present)

The Caribbean Heavyweight Championship became a storyline element again in IWA-PR in November 2022, when Khriz Díaz won an opportunity and criticized that a title that represented Puerto Rico was being contested between foreigners. Vignettes were shown where the challenger traveled to Mexico pursuing Octagón Jr., following provocations in Impacto Total and social media. Sneaking backstage at a AAA card, Díaz ambushed the champion in the lockers and took both the belt and his mask. After Octagón Jr. no-showed a scheduled defense at Histeria Boricua 2023, Savio Vega stripped him of the title and announced that the vacancy would be filled in the event. In a match of impromptu contenders, Díaz defeated Alejandro Marrero to win the revamped belt.