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 Ike
After passing over Inagua, the development of a double eyewall—a feature that usually denotes the beginning of an eyewall replacement cycle—slightly weakened Ike late on September 7. However, the hurricane was able to reintensify and reach Category 4 intensity for a final time before making landfall near Cabo Lucrecia on the coast of Holguín Province in Cuba by 00:00 UTC the next day. Although Ike remained well-defined for most of its crossing of eastern Cuba, the hurricane's core had become disrupted by the time it had reached the Caribbean Sea after spending a few hours over land. Over the next day, Ike tracked westward, paralleling the southern coast of Cuba without much intensification; at times the center of the hurricane was within of the island. At around 14:00 UTC on September 9, Ike made a second Cuban landfall, this time on Punta La Capitana in Pinar del Rio, with winds of . Roughly six hours later, the hurricane emerged into the Gulf of Mexico as a slightly weakened system.