Early career
Owain continued in the service of the Fitzalan earls of Arundel following the end of his education. The earl whom his father had served died in 1377, and was succeeded by his son, also named Richard. Owain's service to the younger Richard Fitzalan is one of the most well-attested periods of his career prior to his rebellion. Before the first records of his service to Arundel, however, Owain appears to have been married to Margaret Hanmer, daughter of David Hanmer. The date of this marriage is disputed. The unreliable nineteenth-century antiquarian William Owen dated Owain's marriage to 1383, but R. R. Davies suggested a date in the 1370s whilst Owain was the ward of her father, drawing a parallel with the marriage of Owain's grandfather Gruffudd Llwyd whilst underage with the daughter of his guardian in 1304.
On 1 March 1384, Owain and his brother Tudur were listed as men-at-arms among the retainers of Sir Gregory Sais, guardian of the town of Berwick-upon-Tweed on the English-Scottish border. Gregory Sais was, according to A. D. Carr, "perhaps the greatest of the Welsh captains of this period" and a close confidant of the Black Prince in the Edwardian phase of the Hundred Years' War. Owain also likely became acquainted during his assignment in Berwick with Henry Percy, Earl of Northumberland and his son Hotspur, who both would feature prominently in his future. In August 1385, King Richard II launched an inconclusive campaign against Scotland which nevertheless razed and plundered its way to Edinburgh. Owain's participation in this campaign is not recorded in contemporary records, but his participation in it is confirmed by his own testimony in the following year. At the age of twenty-seven, Owain was called to give evidence for the High Court of Chivalry on 3 September 1386 in Chester as part of the proceedings of the Scrope v Grosvenor trial. Richard Scrope brought a suit seeking to determine who could bear a coat of arms blazoned Azure, a bend Or against Robert Grosvenor after he saw Grosvenor displaying arms identical to his own on the Scottish campaign; the case lasted for six years. Owain testified that he had seen Grosvenor bear these arms on the expedition in Scotland and that the arms were generally known to be his in Cheshire and Flintshire, as did his brother Tudur, who was then twenty-four. Owain's brothers-in-law John Hanmer and Robert Puleston, the latter married to Owain's sister Lowri, also testified in this trial and were earlier involved in the same Scottish campaign. These men may have served in this campaign in the retinue of the earl of Arundel, or perhaps been mustered directly by Richard II as part of the sizeable contingent from the county palatine of Chester.
Owain and his brother Tudur were mustered in Sandwich on 13 March 1387 as part of the retinue of his old acquaintance, Richard Fitzalan, earl of Arundel. Since 1385, England had been threatened annually by a French naval invasion from Flanders. On 10 December 1386, Richard II had been given a commission to lead 2500 men in a campaign to pre-emptively strike the Franco-Flemish navy commencing March 1387. King Richard had been stripped of his control over England's government in the Wonderful Parliament a month prior, and Arundel was one of the leading opponents of the king, at the centre of the kingdom's political life. Arundel commanded his men in a fleet as admiral, and routed a predominantly Flemish wine fleet sailing home from La Rochelle in the Battle of Margate on 24 March, England's first notable success at sea since the resumption of war with France. The opposing fleet attempted to break through the English navy to Sluis, but was intercepted and forced to fight or beach at Cadzand shore; the battle's spoils included more than 8000 tuns of Poitevin and Saintongeais wine, flooding the English market. Owain was not knighted by Arundel following the battle, though many of his other squires were; this led R. R. Davies to note that though Owain was "by far the greatest of 'the barons of Wales', he could not even make it to the rank of a knight in England".
Owain's father-in-law David Hanmer died in early summer 1387, and by July, Owain had returned to settle the family affairs, just as Arundel began to take action against Robert de Vere, the earl of Oxford and Richard II's favourite. He does not appear to have taken part in any further campaigns under Arundel, as though Owain was enrolled in the earl's retinue at the head of his esquires with the aim of serving in France in 1388, his name was crossed out in the lists, meaning he did not serve. For the next decade, Owain is not mentioned in any surviving records save on 28 June 1397, when the Roman pope Boniface IX granted an indult to Owain and Margaret Hanmer allowing a confessor to grant them plenary remission in the hour of death. J. E. Lloyd, repeated by R. R. Davies, imagined Owain in these years "at ease, wealthy, generous, respected, [and] happy in the life of his home." Ultimately, Owain's hopes for advancement in a military career may have been dashed by the signing of a peace treaty with France in 1389 following Richard II's return to power at Arundel's expense; his other obvious patron, Gregory Sais, died in 1390. No record survives of Owain serving Arundel in an administrative capacity as Gruffudd Fychan served the earl's father, and so the relationship between the two may have at some point cooled.
Though Owain does not appear in traditional historical sources in this period, he was a patron of traditional Welsh poets, including Gruffudd Llwyd and Iolo Goch, a successor to Dafydd ap Gwilym and the leading cywyddwr of his day. Iolo sang three poems to Owain before 1400: one praising his ancestry, one praising him, sung around 1385, and one to his court in Sycharth, sung around 1390. Despite his cognomen deriving from Glyndwfrdwy, Owain's main residence and main source of income appears to have been Sycharth, a moated house in his half of Cynllaith. While Owain's wealth was modest by English standards, he was among the wealthiest of the native Welsh nobility, and may have had an income of up to £70 per annum. Owain himself ordered the construction of the house which hosted Iolo. Iolo's poem praising Owain's ancestry notes his descent from the pre-Conquest princes Rhys ap Gruffudd of Deheubarth, Bleddyn ap Cynfyn of Powys, and Gruffudd ap Cynan of Gwynedd, urging Owain to press his claim to all Powys as his rightful inheritance, while his poem praising Owain himself mentions his service with Gregory Sais in Scotland.
According to Dafydd Johnston, the "most satisfying poem" to Owain by Iolo is Iolo's poem celebrating Sycharth, known by the title "Owain Glyndŵr's Court". The poem describes Sycharth as a moated site ringed by water and approached by a bridge and a single gate, its timber halls raised on four great pillars atop a green hill. Iolo dwells on the symmetry and joinery of the building, likening its coupled roof-timbers and cruciform plan to St Patrick's Cathedral in Dublin and the new cloister of Westminster Abbey, and enumerating nine matching halls, nine wardrobes, a tiled roof and a smoking chimney, and glazed chapels flanking the hall. The surrounding estate is catalogued with equal precision: a watermill, a stone dovecot, a fishpond stocked with pike and sewin, an orchard and vineyard, land producing Owain's food worked by the his serfs, peacocks and herons, a rabbit warren and a deer park, with imported Shrewsbury ale, bragget, wine and white bread on the table. The poem then turns to Owain's family, praising his wife Margaret as the finest of women, generous with wine and mead and noble by birth and disposition, and their children, who come in pairs as a "fine nestful of chieftains", before closing on the openness of the household itself:
Sycharth was the centre of the fertile lands of the eastern half of Cynllaith in the lordship of Chirk, only a mile from the border with England, yet at the time still thoroughly Welsh in character. Owain's share of Cynllaith looked eastward to England: Sycharth lay a mere ten miles from the Arundel castle of Chirk, the market town of Oswestry, and the castles of Whittington and Knockin, the residences of two other Marcher baronial families, the Fitzwarins and the Lestranges, with Chester and Shrewsbury beyond. The fine quality of Owain's home was noted in a letter by none other than Prince Hal to his father Henry IV following its destruction during the rebellion in 1402; the prince described Sycharth as "a well-built house... [with] a fine lodge in his park".