Battle of Villanueva de Barcarrota

When Afonso IV of Portugal learned that Alfonso XI of Castile refused to lift the siege of Lerma, his troops invaded Castile and laid siege to the city of Badajoz, hoping this would force Alfonso XI to lift the siege of Lerma. However, Alfonso XI continued besieging Lerma and sent messengers to Pedro Ponce de León the Elder, Alvar Pérez de Guzmán the Elder and Enrique Enríquez the Younger, noblemen of Castile, asking them to send troops to join Pedro Fernández de Castro "the Warrior", whom he had ordered to go to the aid of Badajoz.^[3]

Alfonso XI also asked for help from the councils of the cities of Córdoba, Seville, Trujillo, Plasencia, Coria and Cáceres, and from Ruy Pérez Maldonado, Master of the Order of Alcántara. These united their forces with those of Pedro Fernández de Castro, and promptly left for Badajoz to aid the besieged town. According to the Chronicle of Alfonso XI, the indiscipline of the troops of Pedro Fernández de Castro was remarkable and his men caused serious damage in the places through which they passed on the way to the city of Badajoz.^[3]

When other noblemen and councils were informed that the city of Badajoz was being besieged by the Portuguese, they readied their troops and prepared to help, even though they had not yet received the messages sent by the King Alfonso XI of Castile. Enrique Enríquez the Younger, lord of Villalba de los Barros and great-grandson of King Ferdinand III of Castile, left the city of Seville accompanied by the men of the Bishopric of Jaén, and went to the Extremadura town of Barcarrota Villanueva, 49 kilometres (30 mi) from Badajoz. He began to harass the Portuguese, preventing them from obtaining supplies. He made inroads into the kingdom of Portugal where he seized much property, livestock and captives.

When Afonso IV of Portugal, who was still besieging Badajoz, learned of the raids that Enrique Enríquez the Younger had made into Portugal, he commanded Pedro Afonso de Sousa, a nobleman of his kingdom, to go to Villanueva de Barcarrota and apprehend the Castilian-Leonese under Enrique Enríquez, and to destroy and burn the town. When the Portuguese troops came in sight of Barcarrota, Enrique Enríquez the Younger and his men sortied from the town, despite being outnumbered. They did not have the opportunity, as the Portuguese made camp on a nearby hill and from there began to make minor attacks against the Spaniards, who, because of their numerical inferiority, did not dare to engage with the Portuguese.^[4]

While the Portuguese and Spaniards remained at a stalemate, the forces of Seville commanded by Juan Alonso Pérez de Guzmán, lord of Sanlúcar de Barrameda, and Pedro Ponce de León the Elder, Lord of Marchena and Bailén, reached the vicinity of Villanueva de Barcarrota. They did not know of the presence of Portuguese troops and were not ready for combat. An individual who had climbed the tower of the church of Villanueva de Barcarrota observed their arrival, realized by the banners they were carrying that they were Castilian-Leonese, and communicated this to Enrique Enríquez the Younger and his men. He told them that if they hurried to attack the troops of Pedro Afonso de Sousa, they could defeat them.

Combat-ready troops under the command of Juan Alonso Perez de Guzman and Pedro Ponce de León the Elder were sent to deal with the Portuguese troops, who promptly fled. The troops of Enrique Enríquez the Younger, who were near the Portuguese, joined the chase before the troops of Juan Alonso Pérez de Guzmán had entered combat. The Portuguese army began to be slaughtered. The Chronicle of Alfonso XI says they were pursued for more than 10 kilometres (6.2 mi). Almost all the Portuguese infantry were killed, and many knights also died. At nightfall the Castilian-Leonese troops returned to Barcarrota. There they learned that troops sent by the council of Cordoba were on the way to Barcarrota.^[5]

When Afonso IV of Portugal, who was still besieging the city of Badajoz, was informed of the defeat of the Portuguese troops in Barcarrota he was disheartened, because the defeat added to the difficulties of conquering the city of Badajoz.

Badajoz was well fortified and well defended by war-hardened men unlike the Portuguese knights, who were not accustomed to fighting. Moreover, the king of Portugal received messengers that told him that Pedro Fernández de Castro "the Warrior" was approaching with his troops to succor Badajoz and that the forces of the council of the city of Córdoba were approaching Badajoz, while the victorious troops of Enrique Enriquez the Younger, Juan Alonso Pérez de Guzmán and Pedro Ponce de León the Elder remained in Barcarrota.

Given the number of enemy troops approaching him, Afonso IV of Portugal decided to lift the siege of Badajoz and return with his army to Portugal.^[6][7]

During his return journey, Afonso IV of Portugal attacked the lands of the Order of Alcántara, since they had opposed him. They defended their territories, but Ruy Pérez Maldonado, Master of the Order, was criticized for his lack of courage against the Portuguese troops.^[8]