Under Henry VII
In 1488 he was on a commission to inspect the ordnance at Calais, and in 1491 was made a knight of the Garter. In the following year he was placed in command of fifteen hundred men sent to aid Maximilian against his rebellious subjects in the Netherlands. The rebels, under the leadership of Ravenstein, held Bruges, Damme, and Sluys, where they fitted out ships to prey on English commerce. Poynings first cleared the sea of the privateers, and then laid siege to Sluys in August, while the Duke of Saxony blockaded it on land. After some hard fighting the two castles defending the town were taken, and the rebels entered into negotiations with Poynings to return to their allegiance. Poynings then joined Henry VII before Boulogne, but the French war was closed almost without bloodshed by the treaty of Etaples on 3 November.
In 1493 Poynings was acting as deputy or governor of Calais; in July he was sent with Warham on a mission to Archduke Philip to gain Perkin Warbeck's expulsion from Burgundy, where he had been welcomed by the dowager duchess Margaret; the envoys obtained from Philip a promise that he would abstain not aid Warbeck, but the duke asserted that he could not control the actions of the duchess, who was the real ruler of the country.
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