Background
He was the third son of Richard Wingfield of Wantisden in Suffolk, and Mary, daughter and coheiress of John Hardwick of Derby, and the sister of Bess of Hardwick.
He was the third son of Richard Wingfield of Wantisden in Suffolk, and Mary, daughter and coheiress of John Hardwick of Derby, and the sister of Bess of Hardwick.
A volunteer against the Spanish in Holland, he was appointed captain of foot in the expedition there of Robert Dudley, 1st Earl of Leicester in December 1585. Wounded action before Zutphen on 22 September 1586, he was knighted by Leicester. Returning to the Netherlands, he was appointed governor of Geertruidenberg.
His position, though, suffered from tension between the English auxiliaries and the States-General.
The garrison lacked pay, and was mutinous. A rumour arose that he intended to hand over the place to the Spanish, and Maurice of Nassau came with a demand for its surrender.
Wingfield denied the imputed treason. But Geertruidenberg was on 10 April, 1589, delivered to the Spanish.
In June 1596 he sailed on board the Vanguard, as camp-master with the rank of colonel, in the expedition under Robert Devereux, 2nd Earl of Essex against Cadiz.
After an attack on the Spanish fleet led by Walter Ralegh, in which he took part, he was one of the first to enter the town. He then feigned a panic-stricken retreat and drew the Spanish back into the arms of a larger hidden English force. In the rout that followed the English broke through the city gates and Wingfield was wounded in the thigh, while Essex and a small band fought through to the plaza.
Unable to walk, Wingfield captured a horse to follow Essex, and—now an obvious target—was killed instantly by a bullet to the head just as the city surrendered.
He was buried five days later with all the funerall solemnities of warre in the cathedral at Cadiz, while the generalls threw their handkerchiefs wet from their eyes into the grave (Stow). In the following year the queen granted his widow an annuity of £100 a year.
Ordered on 21 June to bait an ambush, Wingfield led 200 men along the isthmus leading to the city gates which were defended by 500 Spanish cavalry.
He was a Member of the Parliament of England for Lichfield in 1593. John Donne, a member of the expedition, composed the well-known epigram (Farther then Wingefield, no man dares to go) in tribute.