Ni November 22, 1595, English privateer Sir Francis Drake <unk>with 27 vessels and 2,500 troops<unk> sailed into San Juan Bay intending to loot the city. Sibẹsibẹ, wọn ko lagbara lati ṣẹgun awọn agbara ti o wa ninu awọn odi. Mọ Drake ti kuna lati bori awọn aabo ilu nipasẹ okun, ni June 15, 1598, Royal Navy, ti o jẹ olori nipasẹ George Clifford, 3rd Earl of Cumberland, gbe awọn ọmọ-ogun lati awọn ọkọ oju omi 21 lọ si ila-oorun ni Santurce. Clifford ati awọn ọkunrin rẹ pade resistance Spanish nigba igbiyanju lati kọja afara San Antonio (lati agbegbe ti a mọ loni bi Condado) sinu erekusu San Juan.
Afárá San Antonio