Originally the monument was in the Chantry Chapel, which is now the vestry. The effigy of stone used to be painted red with gold knee and elbow pieces, the surcoat greaves and helmet silver. On the red thigh pieces were golden spots placed at regular intervals, probably represented studs.

Sir John Wingfield, son of Sir Robert de Wingfield a wealthy man of Norman family origin who built the castle and owned much land round it. Friend, confidante and financial adviser to the Black Prince son of Edward III. John founded a college for secular chaplains and a small chapel for masses to be said daily for the souls of the de Wingfields. He was also lord of several neighbouring manorships. At the battle of Poitiers 1355 both he and his ADC Michael de la Pole were involved in negotiations of the sums to be paid as ransoms for the French prisoners . The Black Prince died and at the time of his own death of the Black Death in 1361 he was planning to build a large church at Wingfield.