Battle of Montiel
Fought on 14 March 1369, the Battle of Montiel was the final battle of the Castilian Civil War of Succession. It saw Franco-Castilian forces of Henry of Trastámara waging war against the incumbent, Peter of Castile. The Castilian succession crisis had been of great interest to the English and French, both eager to have Castile as an ally in their own conflict.
Black Prince and the Battle of Nájera
In 1367 an army commanded by the Black Prince had fought in Castile on behalf of Peter of Castile. Peter had promised financial rewards to the Black Prince for his support. With payment and naval support in the Bay of Biscay due following success. The Anglo-Gascon force that had been deployed to assist Peter of Castile was successful. The Battle of Nájera in 1367 handed Peter a huge advantage.
Collapse of the Anglo-Castilian Alliance
However, the Anglo-Castilian alliance fell apart shortly after the Battle of Nájera. Peter of Castile failed to pay. The Black Prince was also unwell, suffering from dysentery on the campaign. With no recompense and failing health, the force from the Principality of Aquitaine left Castile. With it, Peter lost the upper hand in the civil war.
Battle of Montiel
The result was a renewal of campaigning in the name of Henry of Trastámara. Led by the French captain, Bertrand du Guesclin, the army found Peter of Castile at Montiel. The subsequent battle saw du Guesclin demonstrate his tactical flair, using enveloping tactics to secure victory over Peter of Castile’s army.
Peter escaped the battlefield but could only flee as far as Montiel Castle. Here he attempted to bribe du Guesclin, with no success. Instead, he himself was duped into leaving the Castle on 23 March 1369. His half-brother, Henry of Trastámara stabbed and killed him.

John of Gaunt and Constance of Castile
This was not the end of English interest in Castile. Constance of Castile, daughter of Peter, was the second wife of John of Gaunt. The couple married in 1371. Castilian law permitted the husband of a female heir to assume the title of King. Constance had a clear argument to be the rightful Queen. In 1386 it was a claim taken up by John of Gaunt, with the Castilian arms being added to his own and an expedition being launched.
Image Credit
Battle of Montiel. Froissart’s Chronicles. Public Domain, via Wikimedia.