The depression formed on October 31, 1987, in the Caribbean Sea, heading along a northward path into the southern Gulf of Mexico and into Florida until the system was absorbed on November 4.

The depression peaked in intensity with wind speeds of 35 mph (56 km/h) on November 1 with a minimal barometric pressure reading of 1,004 millibars (29.6 inHg).

The depression in the time affected several cities and parishes in Jamaica and Cuba, along with causing significant rainfall in southern Florida.

[2] Prior to the formation of Tropical Depression Fourteen, the southern Caribbean Sea was under a large area of low pressure.

During the period of November 2 and 3, the depression moved to the northeast, crossing over the islands of Jamaica, Cayman and Cuba and then entering the southern parts of the Gulf of Mexico.

[3] On occasion, the convection of the system would flare up, and in the early morning hours of November 3, the Naval Air Station at Boca Chica, Florida reported winds of 50 mph (80 km/h), which would mean the depression may have attained tropical storm status.

[3] In the evening and overnight hours of November 3, the tropical depression continued to the northeast, making landfall in Florida at a location near Tampa Bay.

After emerging from land in the Atlantic Ocean on November 5, the depression had become a low pressure area once again and was last spotted that day near the Carolina Capes.

[7] Wind gusts from Tropical Depression Fourteen exceeded 70 mph (110 km/h) near the Cudjoe Key Air Force Base on November 3.

[10] The significant rainfall caused major damage and issues on the island, with an estimated 1,000+ people being displaced from their homes and being placed into government shelters.