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 Cleo
Moderate to heavy rains fell across Puerto Rico, peaking at 4.95 inches (125.7 mm) at Matrullas Dam. The outer bands of Cleo produced peak sustained winds of 52 mph (85 km/h) at Point Tuna, Puerto Rico. Offshore Puerto Rico on its initial penetration of Cleo on August 23, a Lockheed WC-121N Super Constellation used as a reconnaissance aircraft experienced its port wing tip fuel tank and portion of wing torn away by extreme updraft turbulence, which injured six of its crew. While trying to exit the storm, the starboard tip tank and larger portion of wing were torn away by extreme down draft turbulence. The aircraft was damaged beyond repair. Cleo led to the wettest known 24‑hour period recorded for any site within the Dominican Republic for any month, with 19.99 inches (507.8 mm) falling at Polo. Les Cayes, Haiti was leveled as the storm struck the town. The aircraft carrier U.S.S. Boxer arrived off the coast of Hispaniola on August 29 to provide medical aid and evacuation services to those in the worst impacted areas of Haiti and the Dominican Republic. Damage in Cuba was minimal because the hurricane had weakened and moved through quickly.