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 Maria
Entering the Caribbean Sea, Maria weakened slightly to a Category 4 hurricane due to land interaction with the island of Dominica, however it quickly restrengthened to a Category 5 hurricane and attained its peak intensity with winds of 175 mph (280 km/h) and a pressure of 908 mbar (hPa; 26.81 inHg) at 03:00 UTC on September 20 while southeast of Puerto Rico; this ranks it as the tenth-most intense Atlantic hurricane since reliable records began. An eyewall replacement cycle caused Maria weaken to Category 4 strength before it made landfall near Yabucoa, Puerto Rico at 10:15 UTC (6:15am local time) that day with winds of 155 mph (250 km/h)—the most intense to strike on the island since the 1928 San Felipe Segundo hurricane. Maria weakened significantly while traversing Puerto Rico, but was able to restrengthen to a major hurricane once it emerged over the Atlantic later that afternoon, eventually attaining a secondary peak intensity with winds of 125 mph (205 km/h) on September 22, while north of Hispaniola.