The first book which Caxton written in the Low Countries was The Recuyell of the Histories of Troy, translated by himself from the French original of Raoul Lefèvre. in 1469, he had starts the translation, taken it further at the request of Margaret of York, on 9 September 1471, the Duchess of Burgundy, continued the work in Ghent, and done it in Cologne. This was the first book in English ever to be printed.

The book is a group of stories very freely based on the tales of the Trojan Wars. Caxton planed for a court readership. Stories of war, knightly exploits and love were famous courtly reading. To make sure that his book as well looked appealing to his readers, he had a new typeface shaped, directly based on the handwriting used in manuscripts prepared for the Burgundian court. In all chance the type was created by Johann Veldener, who had as well made Caxton's Cologne type.

While in the Low Countries he wrote another book in English, The Play of Chess. It was as well translated by Caxton himself, from Jean de Vignay’s French translation of Jacobus de Cessolis’s Latin original. This is Caxton’s first dated work, completed 31 March 1474.

The Play of Chess was one more text well-liked at the Burgundian court, an allegory of fixed social structures where every rank has its chosen role. This book was dedicated to George, Duke of Clarence, and the brother of Edward IV and, possibly more prominently, of Margaret of York, who promoted the cause of her favorite brother, the ‘false, fleeting, perjured Clarence’, as he is explained in Shakespeare’s Richard III. Not unexpectedly, given Clarence’s fall from grace, the dedication does not show in the second version of the book dated c.1483.