[7][8] His grandfather, Sir John Wyndham, was implicated in the conspiracy of Edmund de la Pole, earl of Suffolk, and executed for treason in 1502.

In 1539, he was appointed captain of one hundred soldiers and experienced heavy fighting in Ireland under the leadership of James Butler, earl of Ormond.

[2] In December 1547 he sailed two ships to Dundee to support the English garrison at Broughty Castle commanded by Andrew Dudley.

[9] On land, in January he placed a garrison of 20 men with cannon and hand guns on the steeple of St Mary's at Dundee, with the help of Andrew Dudley and the Scottish Lord Gray.

[11] However, near the end of the war, the English commander, the Duke of Rutland, was required to investigate Wyndham's activities capturing foreign merchant vessels in the Firth.

[12] On 29 March 1550, the day peace was declared in England, Wyndham was sent to Scotland with two post horses and five Scottish hostages to exchange for Luttrell, who had been captured at Broughty.

Wyndham wears a powder flask at his neck and a gun over his shoulder inscribed, "TW, aetatis XLII.MDL," indicating he was 42 in 1550.

[15] Thomas Wyndham's crew for this 1553 expedition included a future noteworthy explorer in his own right, Martin Frobisher.