The Siege of Santo Domingo in 1655 was a military effort by English forces against the Spanish stronghold located on the Caribbean island of Hispaniola. At the time, Santo Domingo was of vital strategic importance due to its position along trade routes and its role as the capital of the Spanish Republic of the Indies. The siege was initiated as part of the broader Anglo-Spanish War, which was characterized by territorial disputes and colonial competition primarily over the Caribbean and the Americas. English Commodore Christopher Myngs spearheaded the attack, hoping to secure an essential foothold by capturing this key location.

Upon arriving at Santo Domingo, the attacking force faced stiff resistance from the Spanish defenders. Under the leadership of Don Francisco de la Vega, the Spanish garrison evaluated their defenses and prepared to mount a vigorous defense. This included utilizing the city’s fortifications and natural geography to their advantage, allowing them to effectively hold off the English forces. Despite the initial success in breaching certain defenses, the English found themselves unable to deliver a decisive blow and sustain their campaign due to logistical challenges and mounting casualties.

After seven days of intense fighting, which included failed assaults and attritional strategies, the siege was declared unsuccessful, and Myngs ordered a retreat. The English sustained significant losses that would embolden Spanish resolve in the region and demonstrate the limits of English power projection in the Caribbean theater. The failure of the siege also became a notable event within the dynamics of colonial competition between European powers, highlighting the resilience of the Spanish colonial forces during the mid-17th century.