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.
1979 Atlantic hurricane season
Around midday on September 4, Frederic made landfall in Humacao, Puerto Rico with winds of 50 mph (85 km/h). Flooding on the island forced over 6,000 people to flee their homes in search of shelter. Numerous roads were closed due to landslides and inundation. At least nine cities experienced flooding. After crossing Puerto Rico, Frederic briefly re-emerged into the Caribbean Sea, before making landfall near Santo Domingo, Dominican Republic with winds of 45 mph (75 km/h) at 00:00 UTC on September 6. Minimal impact was reported in that country, though heavy rainfall, exceeding in some places, compounded damage inflicted by Hurricane David. Frederic weakened further while crossing Hispaniola. Later on September 6, the system briefly re-emerged into the Atlantic Ocean, but land interaction with the island weakened it to a tropical depression. The storm crossed the Windward Passage and then made landfall in southeastern Guantánamo Province of Cuba early on September 7. Due to the weak nature of Frederic, minimal impact was reported. It then moved along, or just offshore the southern coast of Cuba. While situated south of Matanzas Province early on September 9, the system re-strengthened into a tropical storm. Despite land interaction with Cuba, Frederic continued to intensify.