In this paper, I attempt to clarify the idea of translation in the British Middle Ages. My questions are twofold: How the translation achieved the status and authority of the source text, and what might be the possible relationship between translation and literature during that period. I begin with the discussion of the Roman theory of translation because it was the Romans who not only first contributed to the theoretical discussion of translation but bequeathed their theories of translation to the British Middle Ages. Particular attention is first given to Cicero whose passing remarks on translation provided the idea of translation as rhetorical recreation, and ultimate substitution, of the source text. Then the theory of translation Jerome proposed is discussed as one with the antithetical relationship with Cicero’s because the Bible translator set his objective in translation in the service of, or supplement to, the source text. My discussion of medieval translation theory is focused on the analyses of the two translations, King Alfred’s version of Boethius’s De Consolatione Philosophiae and Chaucer’s retelling of the Dido Story in his Legend of Good Women. What I suggest in my review of Alfred’s and Chaucer’s translations is both of them admit their roles as a faithful reproducer of the meaning of the source text either in the preface or in the introduction of their works; however, the translation itself betrays the translator’s conscious efforts to compete and excel their source texts. Then the medieval translation, I argue further, reflects the amalgamation of Hieronymic and Ciceronian theory of translation, the former being influential throughout the British Middle Ages and the latter gaining more and more momentum among the vernacular writers, especially during the later Middle Ages in England. From my discussion of the medieval translation, I conclude as the answers to the two questions: A medieval translation becomes an authoritative text like a classical work by means of the translator’s Ciceronian invention of its source(s); There were two kinds of translation in the later Middle Ages in England, a broader one which encompasses sub-categories of Hieronymic and Ciceronian one, the latter of which is considered a literary work in our present view.