Troilus and Criseyde is with 8.239 lines of rhyme royal Chaucer's longest complete poem. It was probably written between 1385 and 1388. Although not a classical story by origin, the matter has a long tradition in European literature. It appears as an episode in The Roman de Troie of Benoît de Sainte-Maure and in Guido delle Colonne's Historia Destructionis Troiae and was developed into a complete story by Boccaccio in his Il Filostrato.

Chaucer's enlarged version of Boccaccio's poem is a very complex poem with psychologically elaborate characters and a considerable philosophical background.

Criseyde is the widowed daughter of Calchas, the Trojan astronomer, who defected to the Greek camp. Troilus, a noble warrior, falls in love with Criseyde and with the help of Pandarus, her uncle and guardian, they begin a secret affair. When Calchas demands the exchange of his daughter for a prisoner of war, Criseyde promises to return to Troilus. She takes, however, the Greek Diomede as a lover. The love-sick Troilus sees Criseyde's betrayal in a dream and wishes to see her with his own eyes. He seeks death in the battle dying in glory. He is advanced to the seventh sphere from where he can observe the world and the transience of life.

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