John is first recorded in 1383 as, with his parents, a recipient of a royal pardon for acquiring the manor of Iden (Sussex) without the King’s licence. As an esquire, he accompanied his father on the naval expedition of March 1387, serving on the flagship of the admiral, Richard, earl of Arundel. However, following Sir Edward’s rise to the position of prominent councillor to Richard II, and (it may be presumed) his consequent detachment from his former place as trusted retainer of Arundel, John became a member of the entourage of Henry, earl of Derby, who at that time was in favour with the King. Shortly after participating in the jousts of St. Inglevert at Calais in April 1390, he joined Derby’s retinue for its journey to Prussia, where, at the siege of Wilna that October, he was promoted to knighthood. It was while they were overseas in the winter of 1390-1 that the earl coveted a gold chain of Dallingridge’s and offered him £6 13s.4d. for it. Sir John’s father was one of the ‘King’s knights’ whom Bolingbroke, at Bishop’s Lynn in July 1392, was to appoint as his general attorneys while he was absent abroad. Sir John probably remained in the earl’s service until Bolingbroke’s departure into exile seven years later.
Sir Edward Dallingridge’s premature death in 1393 left his son faced with a number of obstacles to the secure possession of his substantial inheritance: the Exchequer made demands on him for certain forfeitures for which his father had held responsibility; he was required to confirm his parents’ sale of the Wardieu estates in Northamptonshire; and his paternal grandmother brought a suit against him in the court of common pleas, touching her dower rights in the manor of Bolebrook. Perhaps most damaging were the actions of the duke of Lancaster’s feodary in Sussex, who made distraint on his property for payment of heriot and relief due from Sir John for certain manors; however, having petitioned the duchy council in November 1395, and claimed that he held them merely as a lessee under the terms of a trust set up by his father, he was permitted a limited respite. It may well have been in order to secure protection from the fiscal exactions of Crown and duchy that, in the following January, he made enfeoffments of 11 manors in Sussex and another in Kent, at the same time transferring to friends all his moveable goods (save for five horses and the contents of a single manor-house, which he reserved for his personal use).
Nevertheless, in common with many others of the gentry whose loyalty to the King was suspect, Dallingridge could not remain immune from royal intimidation, especially after Henry of Bolingbroke was accused of treason. In May 1398 he and the trustees of his estates were forced to pay 500 marks to obtain the King’s pardon and exemption from ‘all forfeiture, title, claim, right and interest’ which the Crown might have had in the premises on account of his father Sir Edward’s support for the Lords Appellant several years earlier. It no doubt seemed politic, while Bolingbroke was in exile, for Dallingridge to attach himself to a magnate openly allied with the King; and, accordingly, when he joined the army Richard II took to Ireland in April 1399, it was as a member of the retinue of the King’s half-brother, John Holand, duke of Exeter, then attempting to supplant the dispossessed Fitzalans in their political supremacy in Sussex. But clearly his sympathies remained with his former lord, to whose side he hastened on his return from France to England. Readily welcoming his support, on 18 Nov. Henry IV granted Sir John all the timber felled on the Dallingridge manors of Wilting and Hollington which Richard II had appropriated; and ten days later the new King appointed him as a j.p. Significantly, within three months of the accession he joined the elite group of ‘King’s knights’. Furthermore, Sir John had a friend at the very heart of government, for the new King’s first chancellor, John Scarle, clerk, had been a trustee of his estates for the previous three years. Evidently, King Henry entertained no doubts of Dallingridge’s loyalty even when his brother-in-law, Sir Thomas Sackville II, and his future executor, Thomas Waller, were both arrested on suspicion of complicity in the rising of the demoted duke of Exeter in January 1400; three days after Sir John had stood bail for his friends on 6 Feb., he was granted custody of the lordship of Rotherfield, forfeited by Thomas, Lord Despenser, for his part in that treason; and in the same month he was formally retained by the King for life with a handsome annuity of 100 marks. Dallingridge’s membership of the Household served only to strengthen the King’s fondness for him, and in August 1401 this annuity was all but doubled when the farm of Rotherfield was allowed him for the duration of the minority of Despenser’s heir.
Henry IV always looked with favour on the Beauchamps of Powick, to whom Dallingridge now became related through his marriage to Sir William Beauchamp’s sister. The match also had the advantage of substantially increasing his already considerable income. His own estates in Sussex alone provided him with more than £100 a year; now he could expect perhaps as much as £97 more, derived from the manors of Dassett and Griff in Warwickshire and Sudeley in Gloucestershire, which his wife, Alice, held in jointure from her marriage to Sir Thomas Butler.
During his last Parliament, at Gloucester in November 1407, Dallingridge took out letters patent of exemption from holding further royal offices against his will. Elected to the Parliament on 6 Oct., it would none the less appear that he was in a low state of health, for five days later he made his last will and testament. In fact, he did not survive another year, for he died on 27 Sept. 1408. He was buried in the Cistercian abbey church at Robertsbridge, next to the tomb of his parents, and his executors subsequently paid a ‘great and notable sum’ to ensure that the monks would regularly commemorate the anniversary of his death. His will was proved on 19 Nov.
Sir John left no children. Before his departure overseas four years earlier he had made arrangements that, in the event of his death, his widow Alice was to retain possession of all of his landed holdings for life, with remainder to the sons of his uncle, Walter Dallingridge. The wealthy widow long survived in enjoyment not only of the income from the Dallingridge and Butler estates, but also of a royal annuity of £40. Surprisingly, she never married again; instead, she was called on by Henry V to attend on his French queen and was subsequently employed to look after the infant Henry VI. After her death in 1443, her second husband’s estates passed to his cousin, Richard Dallingridge† (d.1469).