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 Wood, Williams gained his chief instruction in the art of war while serving with Spaniards under the Duke of Alva. The exploits by which he made his earliest fame were achieved in conflict with his alleged tutors in the Low Countries. In April 1572 he joined the band of three hundred volunteers which Captain Thomas Morgan [q. v.] conducted to Flushing to support the cause of the Dutch provinces which had risen in revolt against Spain. Williams proved himself the guiding spirit of the Flushing garrison. But the English met at first with few successes. On Morgan's departure Williams took part with Sir Humphrey Gilbert [q. v.] in August 1572 in what he calls ‘our ignorant poor siege’ of Goes, which ended in disaster for the besiegers. Active hostilities temporarily ceased soon afterwards, and Williams made his way to Germany, where he heard that the Prince of Condé was about to raise an army for carrying on war with Spain. His information proved incorrect, and at Lier in Brabant, on his journey homewards, he fell in with Julian Romero, the best infantry officer in the Spanish service. Romero invited Williams to join his standard, and, in the absence of active hostilities between England and Spain, he consented. He seems to have been treated as a prisoner, and soon returned to his old allegiance. In 1577 he joined the English troops that arrived in the Low Countries under the command of (Sir) John Norris (1547?–1597) [q. v.], and for the greater part of the following seven years acted as Norris's lieutenant. In 1581 a Captain Thomas in the Spanish service challenged Norris to single combat. Norris declined the challenge, but Williams took it up. A duel followed in the presence of the opposing armies. The combatants were evenly matched, and the indecisive engagement ended in a friendly drinking bout (, True Discourse, 1602, p. 38).

Williams's valour attracted attention at home (cf., Elizabeth and her Times, ii. 136). But in 1584 he vainly petitioned the queen for a military position of trust. ‘I would refuse no hazard that is possible to be done in the queen's service,’ he wrote to Walsingham in September of that year; ‘but I do persuade myself she makes no account of me.’ The Spaniards had sought by bribes, he declared, to allure him to their flag. The Spanish generals Parma and Verdugo had begged his countenance. He wished to be true to his country, but if the queen continued to turn a deaf ear to his entreaties, he would be forced to serve Duke Matthias in Hungary, or ‘one of the Turk's bashaws against the Persians’ (Williams to Walsingham, September 1584, in P. R. O.). An anecdote was current in the seventeenth century to the effect that on one of his many attempts to gain the queen's notice at court she, ‘observing a new pair of boots on his legs, claps her hand to her nose and cries “Fah, Williams, I prythe begone, thy boots stink.”’ ‘Tut, tut, madame,’ Williams is reported to have replied with soldierly directness, ‘'tis my suit that stinks’ (Anecdotes and Traditions, Camden Soc. 1839, p. 47). Walsingham showed himself in words at any rate more conciliatory. The minister was as anxious as Williams himself to deal an effective blow against Spain. Williams urged the despatch of a fleet to the Spanish Indies, and in any case rapid and bold action in the Low Countries, where the cause of the protestants was at a low ebb. Williams's importunities at length bore fruit. In 1585 he was sent to the Low Countries with what promised to be an effective English army, under the Earl of Leicester's command.

The effort did not reap the anticipated harvest. Leicester proved singularly inefficient. As of old, Williams was personally conspicuous for his valour, but his exploits produced no permanent result. In June 1586 he and the Dutch general Schenk, with one hundred and thirty English lances and thirty of Schenk's men, made a wild attempt to cut their way at night through the force of Spaniards which was besieging Venloo under the leadership of the Prince of Parma. Williams believed he could enter the city. He and his companions passed through the enemy's lines, slew many Spaniards, and reached Parma's tent, where they killed his secretary. But at the approach of dawn their position was hopeless and they retreated, losing nearly half their number. Two thousand men pursued them, and they found shelter with difficulty in the neighbouring village of Wachtendouk, seven miles distant (cf. Leycester Correspondence, Camden Soc. p. 319). On 2 Sept. in the victorious assault on Doesburg, near Arnhem, Williams was wounded in the arm through his own carelessness. ‘I warned him of it,’ Leicester wrote to Walsingham two days later, ‘being in trench with me [but he] would need run upp and downe so oft out of the trench, with a great plume of feathers in his gylt morion, as so many shotte coming at him he could hardlie escape with so little hurt’ (ib. p. 407). On 22 Sept. Williams took part in the affair before Zutphen, where Sir Philip Sidney was mortally wounded. Leicester wrote to Walsingham on 6 Oct. 1586 (Ouvry MS. fol. 60, copy): ‘Roger Williams is worth his weight in gold, for he is noe more valiant than he is