The underdrawings of both paintings show similar experimental changes made to the composition (or pentimenti), suggesting that both evolved concurrently in Leonardo's workshop.

The composition shows the Virgin Mary seated in a landscape with the Christ child, who gazes at a niddy-noddy used to collect spun yarn.

The earliest reference to a painting of this subject by Leonardo is in a letter of 14 April 1501 by Fra Pietro da Novellara, the head of the Carmelites in Florence, to Isabella d'Este, Marchioness of Mantua.

Leonardo had recently returned to his native city following the French invasion of Milan in 1499; the intervening years he had spent first in Isabella's court, during which brief stay he produced a cartoon (now in the Louvre) for a portrait of her, and then in Venice.

In January 1507 Francesco Pandolfini, the Florentine ambassador to the French court in Blois, reported that “a little picture by [Leonardo’s] hand has recently been brought here and is held to be an excellent thing”.

[7] The composition of the Madonna of the Yarnwinder shows the Christ child twisting his body away from his mother's embrace, his eye caught by her niddy-noddy whose arms (crosspieces) give it the shape of a cross; he precociously recognises it as a symbol of his destiny.

The use of a symbol of the Passion as an object of childish play recurs throughout Leonardo's paintings, appearing for instance in the Benois Madonna and the Virgin and Child with St Anne.

Whereas the background of the Buccleuch version is a watery landscape indifferently painted, that of the Lansdowne Madonna has a dramatic mountain range far more typical of Leonardo.

[13] It has also been suggested that the child learning to walk is the infant John the Baptist, appearing with his mother Saint Elizabeth, as Leonardo would have been unlikely to depict the figures of Mary and Christ twice in the same painting.

This Madonna of the Yarnwinder was bought at auction in Paris in 1756 from a sale of the collection of Marie-Joseph duc d’Hostun et de Tallard, its earliest documented owner.

[17] In 2007 a Chartered Loss Adjuster acting for the Duke of Buccleuch's insurers was contacted by an English lawyer, who claimed that he could arrange for the painting's return within 72 hours.

The lawyer, Marshall Ronald of Skelmersdale, Lancashire, was visited by two undercover policemen who posed as an art expert and an agent for the Duke.

[29] During restoration work in around 1911 the painting was transferred to canvas and several alterations were made, most significantly the removal of a loincloth covering the Child's genitals and the fingers of the Virgin's left hand.

Some include the figure group in the middle ground visible in the Buccleuch and Lansdowne underdrawings; others show the basket of wool described by Fra Pietro da Novellara, though to Christ's side rather than beneath his foot.

Eight paintings, including the copy in the Louvre, show a different kind of rocky outcrop in the foreground from those in the prime versions; many of these are probably by Lombard Leonardeschi.

Both painters were trained in Florence in the first years of the 16th century, and either might be the “Ferrando spagnolo” mentioned as a pupil of Leonardo when the master was working on the fresco of the Battle of Anghiari in the Palazzo della Signoria in 1505.