In the 1990s, Orioles' owner Peter Angelos lobbied the United States federal government to gain permission to hold this series for three years.

Various politicians, including members of the United States House of Representatives, opposed the idea and attempted to block the series.

Eventually, Angelos secured the approval in 1999, after a change in United States foreign policy to Cuba under President Bill Clinton, which eased travel restrictions and increased cultural exchange.

The Baltimore Orioles, who were slated to hold a 1960 exhibition series against the Cincinnati Reds in Havana, moved the games to Miami, Florida.

[5] The United States Department of the Treasury denied Angelos' request on the grounds that American money may not be spent in Cuba under the Trading with the Enemy Act of 1917.

[4][7] Angelos met with Sandy Berger, Clinton's National Security Advisor, to discuss a potential exhibition.

[10] A contingent of United States Representatives, including Ros-Lehtinen, Robert Menendez, Dan Burton, Lincoln Díaz-Balart, and Rick Lazio, lobbied Fehr to try to block the series.

[13] The proceeds of the series were a major sticking point in negotiations, as it violated the United States embargo against Cuba.

[12] Former US diplomat Otto Reich likened the baseball match in Havana to the notion of playing soccer at Auschwitz and also the 1936 Summer Olympics in Berlin, dismissing it as a propaganda ploy by the Cuban government.

The Orioles won the game when Harold Baines hit a single off of Pedro Luis Lazo that scored Will Clark with the go-ahead run in the top of the 11th inning.

[10] A 300-person delegation accompanied the Cuba team, including members of the Cuban media, students, and retired players.

The game was further interrupted by protesters, one of whom ran onto the field during the fifth inning and was thrown to the ground by César Valdez, a Cuban umpire.

Orioles' starting pitcher Scott Kamieniecki, who was on the MLB disabled list at the time, allowed four runs in the second inning to give Cuba the lead.

Calvin Pickering, a rookie first baseman for the Orioles who had been promoted from the minor leagues the day prior, committed three errors.

Six retired players overslept the day after the game in Baltimore and missed their flight back to Cuba, but no other members of the delegation defected.

[26] To discourage defections during the exhibition in Baltimore, Cuba maintained strict security around their young players, not allowing sports agents to speak with them.

[31] Nelson Díaz, a Cuban umpire who officiated the game in Baltimore, defected from Cuba to the United States in 2009.