It was the beginning of the year 1368 and the third year of King Enrique’s reign. In January, the king left the town of Dueñas and went to besiege the city of León. The city itself had sided with King Pedro, whereas the noblemen of the area favoured King Enrique. He built a siege tower at the monastery of Santo Domingo, and, when he fixed it against one of the city towers, those within could no longer defend it; they surrendered the city to him, and everyone went over to his side.

The king left León after winning it and went to attack Tordehumos, which favoured King Pedro, yet it surrendered to him, as did a number of other places. He then decided to travel to Illescas, which is 6 leagues away from Toledo, where the queen, his wife, was staying. There he remained for several days, asking everyone what they thought was the better line of action, whether to proceed through the kingdom or to lay siege to Toledo. Many opinions were expressed on this subject, and finally they agreed to besiege Toledo, owing to the considerable quantity of food that was available in that area. He pitched camp on the plain on 30 April.

Accompanying the king there were up to 1,000 men-at-arms, whilst in the city there were some 600 knights and many foot soldiers. Next, so that the king could intensify his siege of the city, he ordered a wooden bridge to be built across the Tagus, close to his encampment, and sent a number of men-at-arms across it with orders to remain there. As for his wife the queen and the prince, he dispatched them to the city of Burgos, where they could be safe.

In his camp, there was a plentiful food supply and ample monetary support available from those places which the king took while his camp was pitched there, as well as from others round about which were on his side. In order to pay the troops who accompanied him, it was decided that new coins should be struck. Coins were minted and given the name of sesenes, for each one of them was worth six dineros. The coin was minted in both Burgos and Talavera and enabled the king to pay the forces which he had with him.