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.
1932 San Ciprian hurricane
Offshore, the rough seas brought by the hurricane caused heavy damage to shipping as the storm surge caused two boats to run aground near Ceiba. In San Juan, two more boats sustained severe damage. The storm surge and high winds also damaged or destroyed several warehouses. Elsewhere in Puerto Rico, the damage was even more severe as the hurricane's high winds destroyed many homes in outlying villages killing 109 people. The highest death toll came from the town of Rio Piedras which was directly in the path of the hurricane and many of the homes were in poor condition to withstand the hurricane's winds. Damage to roads, power lines, and roads disrupted communications and access to the interior portion of Puerto Rico. Heavy rainfall from the hurricane caused significant flooding that left many homes and buildings under 1.5 feet (0.4 meter) of water.