A third party, Gabriel Castro, helped Huyke with the scouting of organizations which had to pay a thousand dollars prior to being admitted, while independent entities like the Guayama Rotary Club collaborated in raising funds for the teams.

[8] The first Puerto Rican players to play in Major League Baseball, Hiram Bithorn and Luis Olmo, were active in the rosters of San Juan and Caguas.

[10] The All-Star game was scheduled to coincide with the traditional Three Kings Day, an idea suggested by Angel Colon so that the proceeds could be used to buy toys.

[6] In the 1944–45 season, Canena Marquez debuted in the league establishing a record of highest batting average for a rookie with .361, fulfilling the minimum required at-bats.

[10] Jose “Pantalones“ Santiago debuted in this season, earning the Rookie of the Year recognition while Canena Marquez broke Josh Gibson's home run record of 13.

[23] That same year, the LBPPR joined the Caribbean Series, beginning a rivalry with the Cuban League's champion that lasted throughout the next decade, until Cuba ceased to participate in the event.

[27] The players began choosing the league to play due to its competitive level and warm climate during the winter, a custom that has continued until the current decade.

[32] With a roster that also included Luis Olmo, Willy Mays and Ruben Gomez, the Cangrejeros won the 1954–55 championship defeating Caguas in the finals, 4–1.

[36] Juan "Terin" Pizarro won the Most Valuable Player Award, leading the league in wins, ERA, best win-to-loss margin and pitched the LBPPR's seventh no-hitter.

Other changes were experienced in the game's style with the introduction of more player-managers, such as Luis Olmo's, who became the first to consistently employ pitching coaches and closers in the league.

[41] Vic Power used other unusual managing techniques, such as using Frank Howard as a relief pitcher as well as becoming the first player-manager to sit himself in favor of a pinch hitter, replacing his turn in the lineup with Herminio Cortes.

[43] During this timeframe, Puerto Rico expanded its presence in the Caribbean, and a native team frequently played against a representation of St. Thomas and Saint Croix in February.

[51] The following season featured the debut of Jerry Morales who won the league's Rookie of the Year recognition after participating for Puerto Rico's national baseball team in the 1966 Central American and Caribbean Games.

[54] On December 20, 1969, Santurce and Arecibo participated in the only LBPPR game played outside of Puerto Rico, held in the United States Virgin Islands to honor Elrod Hendricks.

[65] The Indios won the title the following season with a lineup that included MVP Kurt Bevaqua and went on to win the Caribbean Series held in Mazatlan, Mexico, Jose Manuel Morales leading all batters with a .421 average.

[72] In 1981–82, the Lobos de Arecibo recessed and their native star players, Edwin Nuñez, Candy Maldonado and Ramón Avilés were drafted by the remaining teams.

[48] The team won the 1983 Caribbean Series, receiving a large welcoming ceremony at Muñoz Marin Airport that included a parade from San Juan to Arecibo.

Maldonado, who became the third native player to hit two home runs in an All-Star game, along with Clemente and Ismael Oquendo, was included in the Series' All Star team after recording a .348 average.

Caguas won the 1986–87 championship, the team went on to win the Caribbean Series, featuring a native lineup that included Alomar, Carmelo Martinez, Edgar Diaz, German Rivera, Henry Cotto, Orlando Mercado and Heidi Vargas.

The 1992–93 season featured the return of Dickie Thon to the league, who led Santurce to a championship over San Juan in the finals as well as the debut of Jose Cruz as a manager.

[71] González had won consecutive batting titles in Major League Baseball and was selected the MVP after recording an average of .333 with seven home runs and 14 RBIs.

The Senadores de San Juan defeated the Cuba national baseball team on December 1, 1993, with a walk-off home run by Javier Lopez.

[86] That year, the Senadores de San Juan managed by Luis "Torito" Meléndez won the title, subsequently assembling one of the strongest teams in the history of the Caribbean Series.

[88] The team was responsible for the only two losses of the Dominican Republic, the country that finished second, scoring victories against Pedro Martínez and José Rijo in the third and sixth games respectively.

[88] Alomar, who had been traded to the team from Ponce for Javier Lopez during the off-season, was named the series' Most Valuable Player after batting 560 with two home runs.

[78] In August 2007, it was announced that the 2007–2008 season was cancelled due to shrinking attendance and profits over the last 10 years, and the league would instead work on a marketing plan and reorganization.

[95] Due to the passing of Hurricane Maria over Puerto Rico in 2017, the league was forced to adopt emergency measures prior to the 2017-18 season, abridging the schedule to one month (being played in January 2018, in order to qualify and being able to defend the Caribbean Series championship), concessions were made to allow Mayagüez and Aguadilla to operate as a single team and changing the rules to play only daytime games due to infrastructure damage and to reschedule games if necessary.

[96] Other changes proposed included the creation of a third team in San Juan, which would feature foreign players in order to market to their diaspora in the city.

In 1995, the Senadores de San Juan managed by Luis "Torito" Meléndez, assembled one of the strongest teams in the history of the Caribbean Series.

[88] The team was responsible for the only two losses of the Dominican Republic, the country that finished second, scoring victories against Pedro Martínez and José Rijo in the third and sixth games respectively.