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 Hortense
By early on September 9, Hortense was upgraded to a hurricane, while curving northwestward. Around 0600 UTC on the following day, the storm made landfall near Guánica, Puerto Rico with winds of 80 mph (130 km/h); this made it the first hurricane landfall on the island since Hurricane Hugo in 1989. Initially, most tropical cyclone forecast models anticipated Hortense would pass south of the island and instead strike the Dominican Republic. After two hours, Hortense emerged into the Mona Passage and brushed the eastern tip of Dominican Republic; Punta Cana near the eastern tip of the country reported the calm of the eye on September 10. Land interaction with Hispaniola weakened the storm slightly, though it would soon re-strengthen.