* 1493: Christopher Columbus arrives in Puerto Rico.
* 1508: Juan Ponce de León founds the city of Caparra, the first permanent European settlement on the island.
* 1521: The Spanish Crown grants Puerto Rico the status of a colony.
* 1765: The British invade Puerto Rico and occupy the island for a year.
* 1898: The Spanish-American War begins.
* 1898: The United States invades Puerto Rico and the island becomes a U.S. territory.
* 1917: Puerto Ricans are granted U.S. citizenship.
* 1950: Puerto Rico becomes a Commonwealth of the United States.
* 1952: The Partido Popular Democrático (PPD) wins the first general elections under the new constitution.
* 1967: The status plebiscite is held, in which Puerto Ricans vote to remain a Commonwealth of the United States.
* 1976: The PPD wins the general elections and begins a 20-year period of uninterrupted rule.
* 1993: The New Progressive Party (PNP) wins the general elections and begins a 12-year period of uninterrupted rule.
* 2005: The PPD wins the general elections.
* 2012: The PNP wins the general elections.
* 2016: The PPD wins the general elections.
* 2019: The PNP wins the general elections.
* 2020: The island is hit by a series of earthquakes, causing widespread damage.
* 2021: Hurricane Fiona makes landfall in Puerto Rico, causing widespread flooding and power outages.