Ralph was 12 years old when his father fell at Shrewsbury and the custody of the family estates as well as his own wardship and marriage was granted by the King to his mother, Beatrice. When he attained his majority Beatrice conveyed to him the manors of Shirley, Hope, ‘Houne’ and Hollington (Derbyshire), Ettington (Warwickshire) and Barnham (Suffolk), on condition that he would pay her 100 marks a year for the rest of her life. She also held a lease from Lord Basset’s feoffees of four of the Basset manors in Leicestershire, on the expiry of which, in 1414, these too passed to her son.
Shirley took as his second wife a daughter of an influential neighbour in Derbyshire, Sir John Cockayne, whose family, like his own, had long served the house of Lancaster. The couple may have been betrothed by 1412, for when Cockayne made a will preparatory to joining the duke of Clarence’s expedition to France, he put the manor of Middleton in the hands of trustees to hold to the use of this daughter, Alice, until the consummation of her marriage. In 1419 Shirley settled on Alice as his wife jointure in the manor of Sheldon (Warwickshire) as well as in other properties, while Cockayne promised them the reversion of his manor of Harthill (Derbyshire). A few years later this alliance between the two families of Cockayne and Shirley was to be strengthened further by Sir John’s marriage to Shirley’s sister, Isabel.
While Shirley’s father had found favour with John of Gaunt and Henry of Bolingbroke, he himself looked for preferment to Henry of Monmouth and, having been knighted on the eve of Henry’s coronation, in January 1414 he secured from him appointment for life as master forester of the honour of Leicester. He contracted by indenture dated 29 Apr. 1415 to serve on Henry’s expedition to France with a contingent of six men-at-arms and 18 archers who were mustered at Southampton on 1 July. Before his departure he made enfeoffments of his estates requiring that, were he to die overseas, the trustees should spend 200 marks for the welfare of his soul and that of his father, and give his sisters, Isabel and Nicola, 200 marks each for their marriage portions and another sister 100 marks for her sustenance, it being understood that they would do nothing without the guidance of his mother Beatrice, who was also made sole guardian of his son, Ralph. In fact, Shirley did come close to death on the campaign: he fell ill at the siege of Harfleur and was sent home with the King’s permission on 5 Oct. Eight of his men returned with him, but the rest went on to fight at Agincourt, on which celebrated occasion one of them (Ralph Fowne) won fame by taking prisoner the duke of Bourbon. Shirley raised a force of seven lances and 23 archers for the invasion of France begun in the summer of 1417, and was present at the sieges of Louviers and Rouen, not returning to England until early in 1419, after the Norman capital had fallen.
During the same period of the 1420s and 1430s Sir Ralph’s grasp over parts of his substantial landed holdings weakened considerably. This was mainly due to the ambitions of Humphrey, earl of Stafford, the heir-general to the last Lord Basset of Drayton. By 1427 Shirley had become aware that his tenure of the two Basset manors in Sheldon was under threat, and not long afterwards he complained in a petition to the King that the earl had dispossessed him of them both and also of Colston Basset (Nottinghamshire), ‘by the procurement and instance of Sir Thomas Chaworth’. Furthermore, Earl Humphrey was ‘proposyng, as yt is comonly sayde’, to enter other of Shirley’s properties in Leicestershire and Nottinghamshire, even though Sir Ralph had ‘with all the menes he cowde’ sued ‘un to the said Erle to have hys good Lordshyp’, and had on various occasions showed Stafford and his council deeds and evidences proving his title to the Basset lands, whereas the earl could produce no such proofs in support of his own claim. Appeals made to the King’s Council and judges as well as to the Commons in Parliament, on the ground that Stafford was ‘of so greate myght that the said besecher is noght of power to sewe agens hym’ at common law, all proved to no avail: by 1436, if not earlier, Sheldon was firmly in the earl’s possession, and by 1438 not only had Colston Basset been lost, but Shirley’s principal seat at Ratcliffe-upon-Soar had also fallen irretrievably into the clutches of his powerful adversary. Towards the end of his life Shirley also had to contend with a revival of the age-old claims of the Erdington family to certain property at Barrow-upon-Soar: in 1442 Sir Thomas Erdington made a forcible entry into the disputed premises and before long secured them at law.
Tradition in the Shirley family has it that Sir Ralph died overseas in 1443, his body being brought back to England for burial in the Lady chapel of the collegiate church in the Newarke, Leicester, ‘in a costly and beautiful tomb’ which also housed the body of his first wife, Joan, removed from its original resting-place at Ratcliffe-upon-Soar. His widow, Alice, quarrelled with her stepson, Ralph, over her dower portion, a matter eventually settled in 1447 by the counsellors of both parties. They died within a few months of each other: Alice in May 1466, leaving as her next heir her son, another Ralph Shirley, and her stepson in December following. The bulk of the Shirley estates then passed to the latter’s son, John (b.c.1427).