Fifteenth‑month internal Castilian siege of Gibraltar, won by Medina Sidonia.
The 1466–1467 Siege of Gibraltar, known as the ninth siege, was a fifteen‑month conflict within the Crown of Castile. Juan Alonso de Guzmán, duke of Medina Sidonia, besieged the royal garrison led by Esteban de Villacreces. The campaign ended with victory for Medina Sidonia and capture of city and castle.
The 1466–1467 Siege of Gibraltar, also called the Ninth Siege of Gibraltar, was a fifteen‑month siege of the city and its castle. It took place in Gibraltar, then part of the Crown of Castile, and was an internal struggle between rival Castilian factions rather than a war with Granada or other powers. After earlier conflicts over control of Gibraltar, Juan Alonso de Guzmán, duke of Medina Sidonia, obtained from the pretender Alfonso a promise of lordship over the city and fortress in return for supporting him against King Henry IV of Castile. In April 1466 Juan Alonso began the siege against the royal garrison commanded by Esteban de Villacreces, lieutenant of Beltrán de la Cueva. Juan Alonso’s forces surprised Gibraltar with a frontal midday assault, broke through the city walls, and forced Esteban to retreat with his men into the heavily fortified castle, where the siege continued. Esteban requested aid from Beltrán and Henry IV but received no reinforcements and relied on local supplies. Juan Alonso later reinforced the siege with additional troops and artillery under his son Enrique, who used cannon to breach the castle’s walls. After prolonged resistance, starvation, and desertions, Esteban surrendered in mid‑1467, giving Medina Sidonia control of Gibraltar.
