At the end of the 16th century, the authorities of Santo Domingo did not have organized nor regular military forces; militias were made up of small garrisons from the fort and by the residents of the villas that would join in the diverse calls to arms. After 1549 a small fleet of galleys was added, but, soon began disappearing between hurricanes and corsair attacks. For a very long time, local functionaries insisted on the need to wall Puerto Plata and Santo Domingo, beginning construction of the wall around the later, but, which, running out of resources was not finished until the 18th century.
After the breakup between England and the Catholic Church in 1533, corsairs and English merchants began to sail the waters of the Spanish Atlantic with more liberty, in spite of the restrictions against it that were still in place.
Charles 1's son, Philip II of Spain, married Mary I of England, who would reinstate Catholicism in England, making Philip King Consort from 1553 to 1558. After Mary's death, Elizabeth I succeeded her half-sister to the throne, and from the start showed political animosity against Spain, permanently establishing Anglicanism and beginning the British colonial expansion. The relationship between Philip II and Elizabeth I deteriorated to the point of declaring war, specially after the English Sovereign financed most of the commercial expeditions, such as Hawkins', financed by corsairs and contraband by some of her subjects throughout the Caribbean.
Knowing that the war was near, Elizabeth authorized Francis Drake , an ex disciple of John Hawkins, to command an armed expedition with instructions of striking the Spanish Empire's possessions in America, attacking the cities of Santo Domingo, Cartagenas de Indias and Saint Agustín in Florida. The population of the city of Santo Domingo, which at this time had 3,500 residents, institutions like the Audiencia, the Archdiocese, University, Cathedral, and other important buildings, found themselves completely defenseless against the enemy's impressive fleet of 30 ships that some fishermen spotted on Friday, January 19th, 1586 around the Punta Caucedo area.
That night, Drake landed a large part of his crew in Haina, which, began their march towards the city at sunrise, helped by black cimarrons of the area, who rapidly became accomplices of the invaders. On January 11th, the English fleet was in front of the Santo Domingo port.
The city's residents attempted to meet the enemy with the small and old artillery that they had, and at the same time sank a few ships at the port's entrance trying to delay the English's access.
Close to the current Guibia beach, a small patrol encountered the English troops coming from Haina. One Spaniard was killed and the rest of the residents fled and hid up river. 150 men concentrated in the fort trying, in vain, to stop the invaders; by the end of the afternoon, the city was under English occupation, and the valiant defenders were forced to abandon the fort that night, sailing up the Ozama river.
The English came prepared to take the great treasure of Santo Domingo, which they imagined would be greater than 400,000 ducats, but accepted 25,000 that they gathered from the residents' personal funds, the King's coffers and the Cathedral's gold and silver artifacts.
Drake and his men pillaged Santo Domingo for a month taking everything of value, the church's bells, all the artillery and merchandise found in the warehouses; burned all the church and civil records, " el monasterio e Yglesia de San Francisco y el monasterio de la madre de dios de la orden de nuestra señora de las mercedes y el monasterio de regina angelovrum de la horden del señor santo domingo e la Yglesia e parroquia de santa barbara y el hospital de san andres y muchas casas del pueblo que casi fueron la mitad”.12 (The San Francisco monastery and church, the monastery of Regina Angelovrum of the order of Santo Domingo and the Santa Barbara church and chapel and the San Andres hospital and around half of the city's houses.)
The hard blow marked the beginning of the economic decline in which the Spanish Santo Domingo would remain until the end of the colonial period or beginning of the 19th century. As correctly indicated by Erdwin W. Palm, "the melancholy of the city, recluse in an past full of grand memories, melancholy characteristic of the antique Antillean capital like any would make province in Europe, was being felt at the end of the sixteenth century."13