|Battle of San Juan (1595)|
|Part of the Anglo-Spanish War (1585)|
Ship entering the bay of San Juan, in front of Fort San Felipe del Morro - view from Isla de Cabras.
|Kingdom of England|
|Commanders and leaders|
Gonzalo Méndez de Cancio|
Sancho Pardo Donlebún
Pedro Suárez Coronel
750 soldiers and sailors,
70 guns 
2,500 soldiers and sailors
|Casualties and losses|
1 frigate burnt,|
40 killed 
8–10 ships sunk,|
400 killed 
The Battle of San Juan (1595) was a Spanish victory during the Anglo–Spanish War. This war broke out in 1585 and was fought not only in the European theatre but in Spain's American colonies.
After emerging from six years of disgrace following the resounding defeat of the English Armada at Lisbon in 1589, Francis Drake embarked on a long and disastrous campaign against Hispanic America, suffering several consecutive defeats there. On 22 November 1595 Drake and John Hawkins tried to invade San Juan with 27 ships and 2,500 men. After failing to be able to land at the Ensenada del Escambron on the eastern end of San Juan Islet, he attempted to sail into San Juan Bay with the intention of sacking the city. 
Unable to capture the island, following the death of his comrade, John Hawkins, Drake abandoned San Juan, and set sail for Panama where he died from disease and received a burial at sea after failing to establish an English settlement in America.
This defeat and the defeat at Pinos ended English hopes of establishing a presence in the Caribbean Sea.
In the first days of 1596 Drake was diagnosed with dysentery, and on 28 January he would die. He became ill most likely during the Puerto Rico campaign, since during the second attack on Puerto Rico an outbreak of that disease killed 400 English soldiers, forcing George Clifford to abandon plans to make San Juan a permanent English base in the Antilles.
- Van Middeldyk p. 68
- The Life of Sir Francis Drake
- Dislates y Disparates sobre el Relámpago del Catatumbo: La expedición de Drake, de 1595, Ángel Vicente Muñoz García, Centro de Modelado Científico, Maracaibo, agosto 2016.
- Konstam, Angus (2008). Piracy: the complete history. Oxford, UK: Osprey Publishing. ISBN 978-1-84603-240-0.
- Van Middeldyk, R. A. (2008). The History of Puerto Rico. Teddington, UK: Echo Library. ISBN 978-1-4068-7497-6.