Tropical Depression Fifteen in 1970 was the wettest known tropical cyclone to affect the United States territory of Puerto Rico. The long-lived depression formed on September 24 just off the west coast of Africa, and for several days maintained a general westward track. It passed through the Lesser Antilles on October 1, and later stalled in the eastern Caribbean Sea. On October 8, the depression crossed over the Dominican Republic, and subsequently it accelerated to the northeast. It was declassified as a tropical cyclone on October 12, although its remnants persisted for another week before dissipating in the westerlies near the Azores.

The Great Hurricane of 1780, also known as Huracán San Calixto, the Great Hurricane of the Antilles, and the 1780 Disaster, is the deadliest Atlantic hurricane on record. An estimated 22,000 people died throughout the Lesser Antilles when the storm passed through them from October 10–16. Specifics on the hurricane's track and strength are unknown because the official Atlantic hurricane database only goes back to 1851.

The 1804 Antigua–Charleston hurricane was the most severe hurricane in Georgia since 1752, causing over 500 deaths and at least $1.6 million (1804 USD) in damage throughout the Southeastern United States. Originating near Antigua on 3 September, it initially drifted west-northwestward, soon nearing Puerto Rico. Throughout its existence in the Caribbean Sea, the hurricane damaged, destroyed, and capsized numerous ships, and at Saint Kitts, it was considered to be the worst since 1772. By 4 September, the storm arrived at the Bahamas and turned northward before approaching the coast of northern Florida on 6 September. The hurricane eventually came ashore along the coastline of Georgia and South Carolina while producing mostly southeasterly winds. A severe gale was noted in New England later that month, on 11 and 12 September, although it was likely not the same system as that which had passed through the Caribbean and southeastern United States earlier that month.
The 1899 San Ciríaco hurricane, also known as the 1899 Puerto Rico Hurricane or The Great Bahamas Hurricane of 1899, was the longest-lived Atlantic hurricane on record, and the second-longest-lived tropical cyclone globally on record after 1994's Hurricane John in the Pacific. It was also one of the deadliest Atlantic hurricanes in recorded history, with an estimated 3,800 fatalities. The third tropical cyclone and first major hurricane of the season, this storm was first observed southwest of Cape Verde on August 3. It slowly strengthened while heading steadily west-northwestward across the Atlantic Ocean and reached hurricane status by late on August 5. During the following 48 hours, it deepened further, reaching Category 4 on the modern day Saffir–Simpson hurricane wind scale (SSHWS) before crossing the Leeward Islands on August 7. Later that day, the storm peaked with winds of 150 mph (240 km/h). The storm weakened slightly before making landfall in Guayama, Puerto Rico with winds of 140 mph (220 km/h) on August 8. Several hours later, it emerged into the southwestern Atlantic as a Category 3 hurricane. The system paralleled the north coast of Dominican Republic and then crossed the Bahamas, striking several islands. Thereafter, it began heading northward on August 14, while centered east of Florida. Early on the following day, the storm re-curved northeastward and appeared to be heading out to sea. However, by August 17, it turned back to the northwest and made landfall near Hatteras, North Carolina early on the following day. No stronger hurricane has made landfall on the Outer Banks since the San Ciriaco hurricane.

The Okeechobee hurricane of 1928, also known as the San Felipe Segundo hurricane, was one of the deadliest hurricanes in the recorded history of the North Atlantic basin, and the third deadliest hurricane in the United States, only behind the 1900 Galveston hurricane and Hurricane Maria. The hurricane killed an estimated 2,500 people in the United States; most of the fatalities occurred in the state of Florida, particularly in Lake Okeechobee. It was the fourth tropical cyclone, third hurricane, and only major hurricane of the year's hurricane season. It developed off the west coast of Africa on September 6 as a tropical depression, but it strengthened into a tropical storm later that day, shortly before passing south of the Cape Verde islands. Further intensification was slow and halted late on September 7. About 48 hours later, the storm strengthened and became a Category 1 hurricane on the Saffir–Simpson hurricane wind scale. Still moving westward, the system reached Category 4 intensity before striking Guadeloupe on September 12, where it brought great destruction and resulted in 1,200 deaths. The islands of Martinique, Montserrat, and Nevis also reported damage and fatalities, but not nearly as severe as in Guadeloupe.

Hurricane Allen was a rare and extremely powerful Cape Verde hurricane that struck the Caribbean, eastern and northern Mexico, and southern Texas in August 1980. The first named storm and second tropical cyclone of the 1980 Atlantic hurricane season, it was the fifth most intense Atlantic hurricane on record in terms of barometric pressure, behind Hurricane Rita, the 1935 Labor Day hurricane, Hurricane Gilbert, and Hurricane Wilma. It was one of the few hurricanes to reach Category 5 status on the Saffir–Simpson Hurricane Scale on three occasions, and spent more time as a Category 5 than all but two other Atlantic hurricanes. Allen is the only hurricane in the recorded history of the Atlantic basin to achieve sustained winds of 190 mph (330 km/h), thus making it the strongest Atlantic hurricane by wind speed. Until Hurricane Patricia in 2015, these were also the highest sustained winds in the Western Hemisphere.
Hurricane Betsy, known as Hurricane Santa Clara in Puerto Rico, was the first North Atlantic hurricane to make landfall in Puerto Rico in 24 years. The third tropical cyclone of the 1956 Atlantic hurricane season, Betsy developed from a tropical wave on August 9 to the east of the Lesser Antilles. It rapidly developed into a 120 mph (195 km/h) major hurricane before striking Guadeloupe. There, Betsy heavily damaged 1000 houses and left severe crop destruction, and there were 18 deaths in the territory. As Betsy continued into the northeastern Caribbean, it capsized a ship, killing its crew of two.

Hurricane Charlie was the deadliest tropical cyclone of the 1951 Atlantic hurricane season. The third named storm, second hurricane, and second major hurricane of the season, it developed from a tropical wave east of the Lesser Antilles. It moved briskly west-northwest, passing between the islands of Dominica and Guadeloupe. It strengthened to a hurricane in the eastern Caribbean Sea, and it struck Jamaica with winds near Category 3 intensity. It strengthened to a peak intensity of 130 mph (215 km/h) prior to landfall on Quintana Roo, Yucatán Peninsula. It weakened over land, and it re-strengthened over the Gulf of Mexico before it made a final landfall near Tampico.

Hurricane Danny in was the first major hurricane to develop between the Lesser Antilles and Western Africa since Hurricane Julia in 2010. The fourth tropical cyclone, and first hurricane of the 2015 Atlantic hurricane season, Danny originated from a well-defined tropical wave that emerged over the Atlantic Ocean on August 14. Traveling west, the system gradually coalesced into a tropical depression by August 18. After becoming a tropical storm later that day, dry air slowed further development. On August 20–21, dry air became removed from the system, and Danny rapidly intensified into a Category 3 hurricane on the Saffir–Simpson hurricane wind scale. Its peak was short-lived as wind shear soon increased and prompted significant weakening. Degrading to a tropical storm by August 23, Danny approached the Lesser Antilles. It degenerated into a tropical wave as it traversed the archipelago on August 24 and was last noted over Hispaniola the following day.

Hurricane David was an extremely deadly hurricane which caused massive loss of life in the Dominican Republic in August 1979, and was the most intense hurricane to make landfall in the country in recorded history. A Cape Verde hurricane that reached Category 5 hurricane status on the Saffir-Simpson Hurricane Scale, David was the fourth named tropical cyclone, second hurricane, and first major hurricane of the 1979 Atlantic hurricane season, traversing through the Leeward Islands, Greater Antilles, and East Coast of the United States during late August and early September. David was the first hurricane to affect the Lesser Antilles since Hurricane Inez in 1966. With winds of 175 mph (280 km/h), David was the only storm of Category 5 intensity to make landfall on the Dominican Republic in the 20th century and the deadliest since the 1930 Dominican Republic Hurricane, San Zenon, killing over 2,000 people in its path. In addition, David was the deadliest Dominican tropical cyclone since the 1834 Padre Ruíz hurricane, which killed over 200 people.

Hurricane Dean was the strongest tropical cyclone of the 2007 Atlantic hurricane season. It was the most intense North Atlantic hurricane since Hurricane Wilma of 2005, tying for eighth overall. Additionally, it made the fourth most intense Atlantic hurricane landfall. A Cape Verde hurricane that formed on August 13, 2007, Dean took a west-northwest path from the eastern Atlantic Ocean through the Saint Lucia Channel and into the Caribbean. It strengthened into a major hurricane, reaching Category 5 status on the Saffir–Simpson hurricane wind scale before passing just south of Jamaica on August 20. The storm made landfall on the Yucatán Peninsula on August 21 at peak intensity. It crossed the peninsula and emerged into the Bay of Campeche weakened, but still remained a hurricane. It strengthened briefly before making a second landfall near Tecolutla in the Mexican state of Veracruz on August 22. Dean drifted to the northwest, weakening into a remnant low which dissipated uneventfully over the southwestern United States. Dean was the second-most intense tropical cyclone worldwide of 2007 in terms of pressure, only behind Cyclone George in the Australian region, and tied with Felix as the most intense worldwide in terms of 1-minute sustained winds.

Tropical Storm Debby was a weak but costly tropical cyclone that affected the Lesser Antilles in September 1994. It was the fourth named tropical storm of the 1994 Atlantic hurricane season; it developed on September 9 east of Barbados. Debby made landfall on Saint Lucia early on September 10, producing heavy rainfall and tropical storm-force wind gusts. The rains caused flooding and landslides, damaging about half of the island's banana plantations. Several villages were isolated after roads and bridges were damaged. Damage totaled about $103 million (1994 USD). On nearby Dominica, Debby damaged crops and fisheries.

Hurricane Dorian caused relatively minor damage across the eastern Caribbean in late August 2019. Originating from a westward moving tropical wave, Dorian organized into a tropical cyclone on August 24 and reached the Lesser Antilles on August 26 as a tropical storm. Turning northwest, the system unexpectedly intensified to a hurricane as it struck the Virgin Islands on August 27. Antecedent to the storm's arrival, local governments across the archipelago issued tropical cyclone warnings and watches, readied public shelters, closed airports, and placed emergency crews on standby. Many of the threatened islands were still reeling from the devastation wrought by Hurricane Irma and Hurricane Maria in September 2017 and fears arose over embattled power grids. In the areas first affected, impacts were limited to gusty winds and modest rainfall. Effects were greater in the Virgin Islands where wind gusts reached 111 mph (179 km/h); however, damage was light. Multiple landslides occurred across the islands and Puerto Rico with only a handful of structures suffering damage. One person died in Puerto Rico while preparing for the storm.

Hurricane Dorian was an extremely powerful and devastating Category 5 Atlantic hurricane, that became the most intense tropical cyclone on record to strike the Bahamas, and is regarded as the worst natural disaster in the country's history. It was also one of the most powerful hurricanes recorded in the Atlantic Ocean in terms of 1-minute sustained winds, with these winds peaking at 185 mph (295 km/h). In addition, Dorian surpassed Hurricane Irma of 2017 to become the most powerful Atlantic hurricane on record outside of the Caribbean Sea. It was the fourth named storm, second hurricane, the first major hurricane, and the first Category 5 hurricane of the 2019 Atlantic hurricane season. Dorian struck the Abaco Islands on September 1 with maximum sustained winds of 185 mph (295 km/h), tying with the 1935 Labor Day hurricane for the highest wind speeds of an Atlantic hurricane ever recorded at landfall. Dorian went on to strike Grand Bahama at similar intensity, stalling just north of the territory with unrelenting winds for at least 24 hours. The resultant damage to these islands was catastrophic; most structures were flattened or swept to sea, and at least 70,000 people were left homeless. After it ravaged through the Bahamas, Dorian proceeded along the coasts of the Southeastern United States and Atlantic Canada, leaving behind considerable damage and economic losses in those regions.

Tropical Storm Dorothy was the deadliest tropical cyclone of the 1970 Atlantic hurricane season. The fourth named storm and fifth tropical storm or hurricane of the season, Dorothy developed on August 17 from a tropical wave to the east of the Lesser Antilles. It tracked west-northwestward throughout its entire duration, and despite forecasts of attaining hurricane status, Dorothy reached peak winds of 70 mph (110 km/) – slightly below hurricane status. The storm struck Martinique on August 20, and subsequently began a gradual weakening trend in the Caribbean Sea. On August 23, Dorothy dissipated south of Hispaniola.

Hurricane Edith brought flooding and wind damage to portions of the Greater and Lesser Antilles. The sixth tropical storm and fifth hurricane of the 1963 season, Edith developed east of the Windward Islands on September 23 from an Intertropical Convergence Zone (ITCZ) disturbance. Initially a tropical depression, it strengthened into Tropical Storm Edith the next day. Shortly thereafter, Edith reached hurricane status. Edith fluctuated between Category 1 and 2 status as it moved west-northwest. Upon reaching Category 2 intensity on September 25, the storm peaked with winds of 100 mph (155 km/h). After striking Saint Lucia on September 25, the storm traversed the eastern Caribbean Sea. Curving north-northwest on September 26, Edith made landfall near La Romana, Dominican Republic, early on the following day as a minimal hurricane. Interaction with land and an upper-level trough caused Edith to weaken to a tropical storm on September 28 and to a tropical depression by the next day. The storm dissipated just east of the Bahamas on September 29.

Hurricane Ella brought flooding to the Greater Antilles and Texas in September 1958. The fifth named storm and third hurricane of the annual season, Ella developed from a tropical wave located just east of the Lesser Antilles on August 30. Initially a tropical depression, it strengthened into Tropical Storm Ella six hours later. The system crossed the Leeward Islands and entered the Caribbean Sea late on August 30. Ella headed westward and by August 31, intensified into a Category 1 hurricane. Hours later, it strengthened into a Category 2 hurricane on the Saffir–Simpson hurricane wind scale. The storm curved northwestward while south of Hispaniola and as a result, struck the Tiburon Peninsula of Haiti on September 1. Flooding in that country killed 30 people in Aux Cayes and left 3 other missing. Additionally, thousands were left homeless, about one-third of crops were washed out, and numerous cattle were killed.

Tropical Storm Erika was one of the deadliest and most destructive natural disasters in Dominica since Hurricane David in 1979. The fifth named storm of the 2015 Atlantic hurricane season, Erika developed from a westward-moving tropical wave while well east of the Lesser Antilles. Hostile conditions, including dry air and wind shear, inhibited significant development, and Erika failed to acquire sustained winds beyond 50 mph (80 km/h). Contrary to predictions of a northwesterly recurvature, the cyclone persisted on a westerly course and passed through the Leeward Islands and emerged over the Caribbean Sea on August 27. Erika succumbed to adverse conditions the following day, dissipating as a tropical cyclone near the Dominican Republic. The remnant system persisted for several more days, ultimately moving across the Gulf of Mexico, before dissipating over Georgia on September 3.

Hurricane Georges was a powerful and long-lived Cape Verde Category 4 hurricane which caused severe destruction as it traversed the Caribbean and Gulf of Mexico in September 1998, making seven landfalls along its path. Georges was the seventh tropical storm, fourth hurricane, and second major hurricane of the 1998 Atlantic hurricane season. It became the most destructive storm of the season, the costliest Atlantic hurricane since Hurricane Andrew in 1992 and remained the costliest until Hurricane Charley in 2004, and the deadliest since Hurricane Gordon in 1994. Georges killed 604 people, mainly on the island of Hispaniola, and caused extensive damage resulting at just under $10 billion in damages mostly in St. Kitts and Nevis, Puerto Rico and Hispaniola.

Hurricane Gilbert was the second most intense tropical cyclone on record in the Atlantic basin in terms of barometric pressure, only behind Hurricane Wilma in 2005. An extremely powerful tropical cyclone that formed during the 1988 Atlantic hurricane season, Gilbert peaked as a Category 5 strength hurricane that brought widespread destruction to the Caribbean and the Gulf of Mexico, and is tied with 1969's Hurricane Camille as the second-most intense tropical cyclone to make landfall in the Atlantic Ocean. Gilbert was also one of the largest tropical cyclones ever observed in the Atlantic basin. At one point, its tropical storm-force winds measured 575 mi (925 km) in diameter. In addition, Gilbert was the most intense tropical cyclone in recorded history to strike Mexico. Gilbert is also

Hurricane Hortense was the first tropical cyclone to make landfall in Guadeloupe and Puerto Rico since Hurricane Hugo in 1989, and the second most intense hurricane during the 1996 Atlantic hurricane season. The eighth tropical cyclone, eighth named storm, and sixth hurricane of the season. Hortense developed on September 3 from a tropical wave in the central Atlantic Ocean.

Hurricane Hugo was a powerful Cape Verde tropical cyclone that inflicted widespread damage across the northeastern Caribbean and the Southeastern United States in September 1989. Across its track, Hugo affected approximately 2 million people. Its direct effects killed 67 people and inflicted $11 billion in damage. The damage wrought by the storm was more costly than any Atlantic hurricane preceding it. At its peak strength east of the Lesser Antilles, Hugo was classified as a Category 5 hurricane—the highest rating on the Saffir–Simpson scale. Over the course of five days, Hugo made landfalls on Guadeloupe, Saint Croix, Puerto Rico, and South Carolina, bringing major hurricane conditions to these and surrounding areas. Lesser effects were felt along the periphery of the hurricane's path in the Lesser Antilles and across the Eastern United States into Eastern Canada. The scale of Hugo's impacts led to the retirement of the name Hugo from Atlantic hurricane names.

Hurricane Iris was the first of three tropical cyclones to affect the Lesser Antilles in a three-week period, preceding the more destructive hurricanes Luis and Marilyn. The ninth named storm and fifth hurricane of the 1995 Atlantic hurricane season, Iris developed from a tropical wave to the east of the Lesser Antilles on August 22 and attained hurricane status within 30 hours. The hurricane weakened to a tropical storm before crossing the islands of the eastern Caribbean from August 26 through August 28. During that time, Iris became one of four active tropical storms in the Atlantic basin. Earlier it had interacted with Hurricane Humberto, and beginning on August 30, Iris interacted with Tropical Storm Karen. Iris re-intensified into a hurricane and attained peak sustained winds of 110 mph (175 km/h) while moving slowly across the central Atlantic. The hurricane accelerated to the north and absorbed a dissipating Karen on September 3. Iris weakened to a tropical storm and became extratropical on September 4, though its remnants reattained hurricane-force winds before affecting western Europe on September 7.

Hurricane Klaus was a minimal Atlantic hurricane that dropped heavy rainfall across the Lesser Antilles in October 1990. The eleventh tropical cyclone and sixth hurricane of the 1990 Atlantic hurricane season, Klaus developed from a tropical wave on October 3 a short distance east of Dominica. It drifted northwestward, and quickly intensified to attain hurricane status on October 5. Though its closest approach to the Lesser Antilles was within 12 miles (19 km), the strongest winds remained to its northeast due to strong wind shear, which caused Klaus to steadily weaken. After deteriorating into a tropical depression, Klaus briefly restrengthened over the Bahamas before dissipating on October 9 under the influence of developing tropical storm, Marco.

Hurricane Luis was a very large, long-lived, powerful and very destructive Category 4 Cape Verde hurricane, as well as one of the strongest and most notable hurricanes of the 1995 Atlantic hurricane season. Luis was also the strongest hurricane to make landfall, and the third-most intense hurricane recorded during the extremely active season. It was the twelfth tropical storm, sixth hurricane, and second major hurricane of the season. At one point, the storm was one of four simultaneous tropical systems in the Atlantic basin, along with Humberto, Iris, and Karen. The storm lasted for 14 days as a tropical storm between late August and mid-September.

Hurricane Maria was a deadly Category 5 hurricane that devastated Dominica, St Croix, and Puerto Rico in September 2017. It is regarded as the worst natural disaster in recorded history to affect those islands and was also the deadliest Atlantic hurricane since Mitch in 1998. The tenth most intense Atlantic hurricane on record and the most intense tropical cyclone worldwide in 2017, Maria was the thirteenth named storm, eighth consecutive hurricane, fourth major hurricane, second Category 5 hurricane, and deadliest storm of the hyperactive 2017 Atlantic hurricane season. At its peak, the hurricane caused catastrophic destruction and numerous fatalities across the northeastern Caribbean, compounding recovery efforts in the areas of the Leeward Islands already struck by Hurricane Irma. Total losses from the hurricane are estimated at upwards of $91.61 billion, mostly in Puerto Rico, ranking it as the third-costliest tropical cyclone on record.

Hurricane Marilyn was the most powerful hurricane to strike the Virgin Islands since Hurricane Hugo of 1989, and the third such tropical cyclone in roughly a two-week time span to strike or impact the Leeward Islands, the others being Hurricane Iris and the much more powerful and destructive Hurricane Luis. The thirteenth named storm, seventh hurricane and third major hurricane of the extremely active 1995 Atlantic hurricane season, Marilyn formed on September 12 as a tropical depression from a tropical wave that moved off the coast of Africa on September 7. After formation, the storm quickly became a tropical storm, and steadily intensified into a hurricane by the time it struck the Lesser Antilles on September 14 at Category 1 strength. Entering the northeastern Caribbean Sea, rapid intensification ensued and it peaked on September 16 north of Puerto Rico as a Category 3 hurricane shortly after it had impacted the U.S. Virgin Islands. A Hurricane Hunter reconnaissance flight reported hail, which is unusual for tropical cyclones. After heading north past Bermuda, Marilyn weakened and became extratropical on September 22. The remnant circulation wandered the Atlantic Ocean from September 23 – October 1, just south of Nova Scotia.

Hurricane Matthew was the first Category 5 Atlantic hurricane since Felix in 2007. Matthew caused catastrophic damage and a humanitarian crisis in Haiti, as well as widespread devastation in the southeastern United States. The deadliest Atlantic hurricane since Hurricane Stan in 2005, Matthew was the thirteenth named storm, fifth hurricane and second major hurricane of the 2016 Atlantic hurricane season. It caused extensive damage to landmasses in the Greater Antilles, and severe damage in several islands of the Bahamas which were still recovering from Joaquin, which had pounded such areas nearly a year earlier. At one point, the hurricane even threatened to be the first storm of Category 3 or higher intensity to strike the United States since Wilma in 2005, but Matthew stayed just offshore, paralleling the Florida coastline.

Hurricane Tomas was the latest recorded tropical cyclone on a calendar year to strike the Windward Islands. The nineteenth named storm and twelfth hurricane of the 2010 Atlantic hurricane season, Tomas developed from a tropical wave east of the Windward Islands on October 29. Quickly intensifying into a hurricane, it moved through the Windward Islands and passed over Saint Lucia. After reaching Category 2 status on the Saffir-Simpson scale, Tomas quickly weakened to a tropical storm in the central Caribbean Sea, due to strong wind shear and dry air. Tomas later regained hurricane status as it reorganized near the Windward passage.