Woodward, Rowland (bap. 1573, d. 1636), poet, secretary, and scribe, was baptized on 23 August 1573 presumably in London, though the precise location remains unknown. He was the son of John Woodward (b. c.1553), a vintner of St Mary-le-Bow, London, and Margaret Bulstrode (1522–1560); his paternal grandfather was John Woodward (1538–1566) of Upton, Buckinghamshire. Rowland Woodward is best known as a friend of the poet John Donne. He and his brother Thomas Woodward (bap. 16 July 1576) exchanged verse epistles with Donne in the 1590s, and Rowland later transcribed one of the most important contemporary manuscript collections of Donne's poetry, the Westmoreland manuscript.

Woodward entered Lincoln's Inn on 21 January 1591, where Donne was admitted in May 1592 after a year at Thavies Inn. The friendship must have endured for at least two decades, since Donne presented Woodward with his prose tract Pseudo-Martyr, printed in 1610 (now Bodl. Oxf., MS Arch. H e.83). In addition to his legal studies, Woodward apparently trained himself as a linguist before entering Sir Henry Wotton's service as a secretary about 1604–5. Wotton deemed him 'a very honest person & of a very capable spirit, besides being furnished at home by his own industry with good beginnings of the French, Italian, and Spanish languages; whereof he spoke the last best' (L. P. Smith, 1.326). Three occasional poems also demonstrate Woodward's abilities in Latin: on the death of Sir Edward Rosseter in November 1605 (Northants. RO: MS Westmorland (A) 6.vi.1, fol. 12v), on Sir Nicholas Smith's death in 1622 (TNA: PRO, SP 16/540/441), and on the comparative merits of Venice and Amsterdam (TNA: PRO, SP 16/540, fol. 438r). In later life Rowland would claim that he was 'never given' to a 'poetical vaine' (TNA: PRO, SP 16/171, fol. 34).

During Wotton's 1605 embassy to Venice, Woodward was sent to Milan to gather intelligence (BL, Cotton MS Julius E, ii, 87), on the pretext of improving his Spanish. One evening he was dragged from dinner by forty men and imprisoned by the Inquisition. He was released four days later on the orders of Count Fuentes and, his cover now blown, recalled to Venice. Despite this lucky escape, great misfortune befell him in 1607: 'assalted by theeves' in Champagne while delivering dispatches from Italy to England, he was 'left for dead upon the place, with many great wounds receaved' (TNA: PRO, SP 16/8/87, fol. 142). Thomas received £60 compensation for his brother's 'surgeons and diets' in February 1608 (Devon, 54–5), and in 1610 Rowland received £1000 reimbursement towards debts accumulated in Wotton's service (BL, Add. MS 12497, fol. 151v). Wotton ‘placed’ Woodward in the service of Thomas Ravis, bishop of London in 1608 (L. P. Smith, 420). However, Woodward was still suffering from 'the grief of a maime' as late as 1625 (ibid., 481) and it seems the trauma stayed with him throughout his life. In July 1620 he mused: 'it is the nature of men that have bene wounded, to discourse willingly of their hurts, and take the least occasion to show them' (TNA: PRO, SP 14/116/1, fol. 1r). Similarly, a professional set-back in 1630 provoked thoughts of physical assault: 'I could put on no armor of defense, & stand upon my guard … I feele a sorenesse & debility in all my parts' (TNA: PRO, SP 16/169/4, fol. 9).

Woodward was friends with Sir Francis Windebank, whose sister he tutored in poetry and Italian (TNA: PRO, SP 14/115/21, fol. 29); corresponding with Windebank between 1627 and 1631, frequently summarizing foreign news, he complained about the lack of financial reward in Wotton's service, and enclosed a poem, now lost, on the birth of the future Charles II (TNA: PRO, SP 16/171/23). George Villiers, the future first duke of Buckingham, tried to have Woodward posted to Brussels in 1615 to accompany the diplomat William Trumbull. Woodward may instead have travelled to Venice as Wotton's secretary from October 1615 to August 1619 (Bell, 290), and still spoke of Wotton as a patron in the early 1620s.

Scattered references to Woodwards in early seventeenth-century England may refer to Rowland, Thomas, or another man: among gentlemen of the privy chamber in 1611; among clerks of the cheque in 1612; and in a Donne letter of March 1614 (Donne, Letters to Severall Persons, 170). From the 1620s Rowland Woodward resided in Gardener's Lane, Westminster, served as secretary to Sir Dudley Digges on a journey to the Low Countries (Nov 1620–Feb 1621; Huges and Kennett, 2.655), and had befriended Sir Thomas Roe by 1622, if not long before. Rowland's sister may have lived with him in the 1620s, since he regularly appends her good wishes to the Windebanks. Woodward travelled to France with members of the Fane family between 1622 and 1625, a journey that exhausted him, although he maintained strong professional ties to the Fanes (TNA: PRO, SP 78/74, fols. 1–2; SP 78/74, fols. 82–3). On his return he asked the king for a pension in recompense for 'losse of much blood in his late m^ties. Service' (TNA: PRO, SP 16/8/87). In 1630 he lost a coveted position in the signet office, acquired for him by Windebank; the blow was alleviated by an appointment as deputy master of ceremonies to Sir John Finet, and by the significant emotional support of Woodward's wife. Three years earlier, on 5 January 1627, Rowland had been granted a licence to marry Eleanor, daughter of Henry Grimsditch (Grymsditch, or Grymesdiche) in Bridewell (Chester and Armytage, 182). Eleanor's age was recorded as thirty-two, and she was 'at her own dispose'. Windebank, who was related to the Grimsditch family, may have made the introduction. Interestingly, Woodward did not appear himself for the licence, as was usual, but was represented instead by John Barker, apparitor to the bishop of London (LMA, MS 10091/11, fol. 63v).

Rowland Woodward is generally accepted as the addressee of five verse epistles by John Donne for which each of the given dates is conjectural. All of the verse epistles are traditionally headed 'To Mr. R. W.', beginning: 'Muse not that by thy mind thy body is led', 'Zealously my Muse doth salute all thee' (both early 1590s), 'Kindly I envy thy Songs perfection' (c.1593–4), 'If as myne is thy life a slumber bee' (August 1597), and 'Like one who in her third widowhed doth profes' (1597–9). Woodward's brother Thomas was sent four verse letters, usually headed 'To Mr. T. W.': 'At once from hence my lines & I depart' (1588–90), 'All haile sweete Poet, more full of more strong fyre' (1590–92), 'Pregnant agayne with th'old twins Hope & Fear' (1591–2), 'Hast thee harsh verse as fast as thy lame measure' (1592–4). Thomas may have prompted Donne's first poetical uses of daring theological wit (see, for example, 'Haste thee', 6), and the poems he received are also notable for a distinct homoerotic strain. Donne's poems imply that both brothers also sent him verse. One unattributed poem entitled 'To M^r J: D.' ('Thou sendst me prose & rimes') is assumed to be by Thomas.

The verse epistle 'Like one who' indicates that by the end of the sixteenth century Rowland knew of Donne's 'love song weeds' and 'satirique thorns' (5)—that is, the elegies (and perhaps also other erotic verse) and satires. Indeed, Rowland collected a substantial body of Donne's work, as attested by his transcription, probably about 1620, of the Westmoreland manuscript (NYPL, Berg collection), one of the most authoritative surviving witnesses of Donne's poems (and some prose). The manuscript was compiled for and owned by Francis Fane, first earl of Westmorland, another Lincoln's Inn contemporary, for whom Woodward acted as secretary. This collection of 79 poems and 10 prose paradoxes contains all 5 satires, 13 elegies, 19 holy sonnets (including 3 preserved here uniquely), 20 epigrams, and some other genres, but only one of the Songs and Sonnets ('A Jet Ring Sent'). It is suggested (Cain) that Woodward's introduction of Donne's as yet unpublished verse to Apethorpe, the Fanes' Northamptonshire seat, may have directly influenced the poetry of Mildmay Fane.

Woodward, the owner of a travelling library, also collected books. H. R. Woudhuysen listed twenty-eight known volumes in 2012, and has since been alerted to fourteen more (private information). Woodward's Spanish motto, 'De juegos el mejores con la hoja', is often present on the title pages. This can translate as 'Of all games, the best is with the leaf', possibly punning on the ‘leaf’ suit in the game of cards (equivalent to spades), and the leaves of a book. Other meanings of juegos (‘services’) and hoja (‘blade’) might imply that Woodward conceived of his service to the state as intellectual rather than martial. He received volumes from William Hakewill and William Laud (now Folger, HH 130/38), and himself gave a book of 1629 on coastal defences to Ben Jonson.

Woodward's books were incorporated into the Westmorland collection at Apethorpe, where he died in 1636. By this date he was earning a steady 6s. 8d. from the lord chamberlain for his 'attendance upon ambassadors and strangers' (CSP dom., 1636, 356), a role subsequently occupied by Sir Balthazar Gerbier. He was survived by his wife who erected an alabaster monument to 'Rowlandus Woodward Armiger' in the chancel of St Leonard's church at Apethorpe, inscribed with an epitaph of his own composition (Deas, 457).