On 25th March 1367, John of Gaunt, lord of Pontefract, rallied the Anglo-Gascon army at Vitoria, northern Spain, to repel the forces of Enrique of Trastamara (later King of Castile and León) and his brother Tello who had overrun the camp of Sir Hugh Calveley. The Black Prince’s forces together with those of Sir John Chandos came to the aid of Gaunt to assist in warding off Tello.

On 14th February 1367, John of Gaunt, Duke of Lancaster and lord of Pontefract, together with Sir John Chandos, led the Black Prince’s vanguard across the Pyrenees through the pass of Roncesvalles. The 17 miles’ (27 km) crossing had to be made in the nine available hours of daylight with a climb of over 4,000 ft (1,220 metres) in full military equipment and fast-changing, winter weather. The Black Prince’s section of his army could not attempt the crossing for a further six days, with the main body of the army reaching Pamplona, the capital of the kingdom of Navarre on 23rd February.

On 10th October 1361, John of Gaunt, lord of Pontefract, attended the marriage of his brother, the Black Prince, to Joan, Countess of Kent, at Windsor; the Pope had given his assent to the union as Edward and Joan were related in the second and third degree.

On 14th April 1361, the Black Prince attended Henry of Grosmont’s, lord of Pontefract, funeral at the Newarke (Leicester) and placed two pieces of golden cloth on the bier.

On 8th May 1360, a treaty was agreed between England and France at Brétigny, near Chartres after negotiations between Henry of Grosmont, lord of Pontefract, and French ambassadors. Its terms were modelled on an earlier agreement between Edward III and King John II at London in May 1358 with Edward renouncing his claim to the crown of France and former Plantagenet possessions of Anjou, Maine, Touraine and Normandy. In return, Edward would hold Aquitaine, Ponthieu, Calais and Guînes ‘in all freedom and perpetual liberty, as sovereign lord and liege and neighbour to the king and realm of France, without recognising the king or crown of France as sovereign over him, nor paying him homage, showing obedience or being in subjection to him.’ King John’s ransom was reduced to 3 million gold crowns (nearly £360 million in today’s money).

On 11th October 1370, the ailing Black Prince appointed his brother, John of Gaunt, Duke of Lancaster and lord of Pontefract, as his lieutenant in Aquitaine after Gaunt had participated in the siege of Limoges even engaging in hand-to-hand fighting in the undermining tunnels. The Black Prince then returned to England leaving his brother in charge.

On 7th January 1397, seven-years-old Isabella of Valois, wife of Richard II and eldest daughter of Charles VI of France, was crowned Queen of England, the day after her husband’s thirtieth birthday.

During the Parliament of January 1394, John of Gaunt, lord of Pontefract, petitioned for his son, Henry of Lancaster, to be the king’s heir claiming preposterously (some say) that his first wife Blanche’s great-grandfather, Edmund (Crouchback) of Lancaster, had been the true elder son of Henry III but had been overlooked in favour of his brother Edward I on account of Edmund’s physical deformity. This would have made Edward I’s nephew, Thomas of Lancaster, the next rightful king and thereafter his descendants. The nonsensical nature of this line of reasoning was apparent in not only Edward I having been over five years older than his brother, Edmund, but that it would have invalidated John of Gaunt’s own high rank and status as a true king’s son.

In May 1389, Richard II, then twenty-two, later to be Pontefract Castle’s most famous prisoner, declared himself of age, thereby able to rule in his own right.

On 27th July 1380, Richard II granted Mary de Bohun’s marriage to John of Gaunt’s (lord of Pontefract) son, Henry of Lancaster for 5,000 marks (£2.5 million today). Gaunt was excused this sum as he was owed at least as much for his war ‘expenses’. The marriage would take place seven months later.