Hobildod’s putative father, who served as a coroner in Cambridgeshire in the 1370s and early 1380s, probably held property at Tadlow, where he himself came to own a sizeable moated manor-house. This contained, from 1408, a private oratory allowed by special licence granted to John and his wife by the bishop of Ely. Nevertheless, Hobildod’s landed holdings at Tadlow were of comparatively little value: in 1412 they were estimated to provide him with an annual income of no more than £2, and it was the annuities earned by him in the service, first of John Holand, earl of Huntingdon, and then of Henry IV, which afforded him the expectation of being able to spend £20 a year more.
Hobildod evidently first came to public attention for his prowess on the tournament field. In May 1388, already retained by Richard II as a ‘King’s esquire’, he was issued with a royal licence to sail with Lord Beaumont and Sir Peter Courtenay to Calais, there to perform feats of arms against the French. Such activities earned him occasional rewards from the King, including a gift of £20 forfeited from the former Bealknap estate in 1392, but he was to benefit more in the long term from the patronage of Richard’s half-brother, the earl of Huntingdon. In January 1393 he was associated with certain of the earl’s followers from the West Country, among them Robert Cary, in standing bail for John Windsor, executor of the will of William, Lord Windsor, who had been imprisoned in Newgate at the suit of his kinsman’s widow, the notorious Alice Perrers. This was no light undertaking, for the penalty for Windsor’s failure to appear in court was set as high as £8,000. Hobildod joined the King’s expedition to Ireland in April 1399 as one of those in the company of Holand, by then created duke of Exeter.
Despite his apparently secure position as a royal retainer, Hobildod was beset with financial difficulties. The last two years of Henry IV’s reign saw him engaged in a number of lawsuits involving substantial sums of money. He and his associate, John Teversham, were forced to sue various debtors for amounts totalling £180, and at the time of the Parliament of 1411 he was having to defend himself in the courts of London on charges of debt brought by such creditors as (Sir) Rustin Villeneuve, William Cromer and a goldsmith named Albert Vanandirnake. Hobildod obtained official confirmation of his royal annuity following Henry V’s accession and was ready to fulfil the military obligations tacitly implied in his retainder when the time came, not least because he would thus obtain temporary respite from defending himself at law. Thus, he contracted on 29 Apr. 1415 to serve in France with two archers, and he also spent three months from 22 June 1416 in the naval force engaged for the relief of Harfleur. Earlier in 1416, he had secured royal pardons of the outlawry resulting from his failure to appear in court to satisfy Sir John Howard for the sum of £8, due on a bond made four years earlier, and also a draper and two mercers from London for debts amounting to £16 12s. Hobildod does not seem to have joined the King’s second expedition to France in 1417. His name, however, appeared on the shortlist of those able to do military service in the defence of the realm, which the j.p.s for Cambridgeshire sent to the royal council in January 1420. He is not recorded after attending the shire elections held at Cambridge for the Parliament of May 1421.