The first and oldest monument is that on the north wall to the west of the vestry door. The figure of the knight, which is six feet five inches in length from the top of the helmet to the point of the feet, is carved in stone and was originally painted. He wears on his head a close-fitting bascinet of the period of the latter part of the 14th century. His head rests on his helmet which is broken and defaced and at his fee is a lion which is now in two pieces.
Sir John was the son of Robert de Wingfield, a wealthy man of a family of Norman origin. Sir Robert left his title and lands to his eldest son John who was in the army fighting in France. John was a confidante and financial adviser to the Black Prince, son of Edward III and heir to the throne.
While at Wingfield Castle, Sir John proposed to found a College for secular Chaplins and a Collegiate Church. In 1361 Sir John died of the Black Death leaving a widow Alianore and only child Katherine.
In 1362, in memory of her husband, Alianore arranged for the building of Wingfield College together with a large Collegiate Church. It was stated that the church in order to make it suitable for the College must be constructed "with a belfry, bells, chapels, at a very great expense". The Chancel was built first and then the chapel to the side with the tomb of the founder.
Sir John`s daughter, Katherine, married Michaael de la Pole, 1st Earl of Suffolk.