1899 San Ciriaco hurricane
Hurricane San Ciriaco set many records on its path. Resulting in at least 3,369 deaths in Puerto Rico, the storm was the deadliest hurricane to hit the island and the strongest at the time, until the Hurricane San Felipe Segundo made landfall in 1928 as a Category 5 hurricane. It was also among the deadliest Atlantic hurricanes ever recorded.
Hurricane Betsy (1956)
Hurricane Betsy, known as Hurricane Santa Clara in Puerto Rico, was the first North Atlantic hurricane to make landfall in Puerto Rico in 24 years. The third tropical cyclone of the 1956 Atlantic hurricane season, Betsy developed from a tropical wave on August 9 to the east of the Lesser Antilles. It rapidly developed into a 120 mph (195 km/h) major hurricane before striking Guadeloupe. There, Betsy heavily damaged 1000 houses and left severe crop destruction, and there were 18 deaths in the territory. As Betsy continued into the northeastern Caribbean, it capsized a ship, killing its crew of two.