This woodcut appears in the text at the moment when Giuliano, who had previously devoted himself entirely to hunting and mocked the folly of lovers, beholds the beautiful Simonetta for the first time. That the two figures appear on a cloud suggests the delusive nature of the appearance that transforms Giuliano from a hunter into a captive of love. By conjuring up a phantom doe, Cupid had lured the young noble to the place where he met Simonetta.

The "beautiful nymph," with her graceful contrapposto pose and flowing garments that recall depictions of nymphs and bacchantes in ancient Roman relief sculpture, is probably inspired by the art of Botticelli. The great painter of the Florentine Renaissance had created the banner that Giuliano carried at the joust of 1475, on which Simonetta was represented in the guise of Minerva binding Cupid—a figure of chastity.

Awakening from a bewildering dream, Giuliano prays to Minerva, under whose guise his beloved had appeared to him in the dream, for the strength to win the joust and thereby conquer his fair Simonetta. Although he thinks he is praying to Minerva, the statue is clearly labeled Cythera, one of the names by which Venus is known. It is Venus who has caused his dream and it is for Venus and Cupid that he will fight in the joust. The book ends prematurely at this point, having never been completed by Politian.

Three years after the joust, both lovers were dead, Simonetta of an illness and Giuliano of an assassination plot.

This early edition of the Giostra was published with Politian's Orpheo, a courtly entertainment written at the request of Cardinal Francesco Gonzaga during Politian's stay in Mantua (1478–80). In the dedication, the poet apologizes for the play's imperfections, noting that it was composed in two days and written in Italian in order to be understandable to the spectators. The narrative follows Ovid's account, but is set within a pastoral framework inspired by Virgil's Eclogues. Here we see, at left, Orpheus taming the wild beasts with his playing, while at right shepherds converse. One of the shepherds, the young Aristeo, is hopelessly in love with Eurydice, who is about to wed Orpheus. Aristeo will chase Eurydice through the woods, where she will be fatally bitten by a snake.