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.
1876 San Felipe hurricane
The minimum pressure that was measured in San Juan was about in the morning, with winds up to about 60 mph and rain at around . The hurricane maintained this intensity and made landfall on the eastern side of Puerto Rico. Shortly after landfall, the hurricane rapidly weakened to a Category 2 hurricane, then to a Category 1 hurricane after reemerging in the Atlantic. Again maintaining strength, the hurricane made landfall on the eastern tip of Dominican Republic with winds of 80 mph.