Damage was heaviest in Jamaica where it caused $300,000 (1987 USD) to utitlites, roads, agriculture and health. Floods put villages and towns underwater and washed out roads/bridges. Landslides caused 279 roads to be closed off. The most affected parishes in Jamaica were Clareon, Saint Catherine, Kingston, Trelawny and Saint Arew. The towns of Crooked River, Riversdale and also the rivers: Rio Minho and Rio Dogna also experienced damage. The damage was comparable to the flood in June of the prior year.
The depression continued to the northwest, though convection remained intermittent and sporadic. While passing to the west of Key West on November 2, a convection burst occurred, resulting in strong winds across south Florida and the Florida Keys. The Naval Air Station at Boca Chica Key, for example, reported east winds of 45 mph (72 km/h) with gusts of up to 65 mph (104 km/h). In a feeder band, a Reconnaissance Aircraft flight experienced severe turbulance and recorded winds of 92 mph (147 km/h) with a pressure of 998 mbar. It is unknown if the depression briefly attained tropical storm status because convection quickly diminished. The weak swirl of the tropical depression turned to the northeast and made landfall near Tampa Bay on the 4th. Shortly after making landfall, it merged with a weak extratropical low, and accelerated to the northeast.
Tropical Depression Fourteen peaked at 35 mph with a minimal pressure of 1004 mbar, but many readings say that Fourteen may have been a tropical storm.
Wind gusts reached in excess of 70 mph at the Cudjoe Key Air Force Base at 312 UTC, which is a maximum tropical storm. Sustained winds in the same area were at 50 mph. Boca Chica Key reported a peak gust of 65 mph with maximum sustained winds of 50 mph, the same area as a pressure reading of 1005.0 mbar was recorded. Cuba reported sustained winds of about only 25 mph recorded at 900 UTC on November 3 in Havana. However, no gust reports were recorded. Kingston, Jamaica reported a peak gust of 58.65 mph on October 31 with sustained winds of about 45 mph. Several ships reported tropical storm winds, peaking at 60 mph with sea levels of 32½ feet and swells of 24½ feet.
While passing to the west of Jamaica, the depression dropped heavy rainfall on the island, prompting officials to issue flash flood warnings. Over a 3-day period, Kingston recorded a total of 10.21 inches (25.93 mm), the highest daily rainfall total being 6.38 inches (16.21 mm) on November 1. Over 1000 people in Jamaica were displaced from their homes and put in shelters. Residential areas in several towns and villages were underwater. Landslides and floodwater caused major damage to roads in Jamaica, but most were restored soon afterwards. Jamaica reported that three bridge washouts from heavy rainfalls. $52 million (1987 JMD) of damage was done to roads, not including the bridges. $1.5 million was done to utilities, $74 million to agriculture and $33 million to health. The damage totaled out to $160.5 million (1987 JMD).
Similarly, Cuba reported moderate rainfall, peaking at 4.75 inches (12.07 mm) in Bahia Honda, Cuba, 2.03 inches in Havana and 2¾ inches in Saua La Grande. Despite being a very weak system, the depression also dropped moderate precipitation across Florida, peaking at 10.23 inches (26 mm) at Loxahatchee National Wildlife Refuge. Miami reported about 4.42 inches and as high as 5.9 inches in Tavarnier. Rainfall over one inch was experienced as far north as eastern Georgia and extreme southern South Carolina.Mississippi and Alabama also recored about 1 inch of rain. Rainfall less than 1 inch, however, went unrecorded.
Damage was minimal, if any was experienced. According to an unofficial report, the flooding caused six fatalities in Jamaica. There are no other reports of casualties or damage from the system.