In this paper we examine a number of linguistic traits in Ieuan ap Hywel Swrdwal's English-language poem entitled "Hymn to the Virgin" (circa. 1480). These are compared to similar features portrayed in the speech of captain Fluellen, on of the main characters in Shakespeare's play, Henry V (1599). While Swrdwal's poems in perhaps the first attested example where Welsh English characteristics are highlighted for nationalistic reasons, Shakespeare intention is clearly to caricature the Welsh accent in English for the pleasure of his audience. The approach used here is sociolinguistic and diachronic. The working hypothesis based on the principle that the English and Welsh languages have exercised mutual influence on each other since the two languages have been in contact, that is to say for well over a millennium. This linguistic interaction has provoked, and continues to provoke, significant changes that have altered Welsh English has well as the Welsh language itself. We thus have two highly symbolic examples of Welsh English, the first as viewed from the inside by a Welshman and the second as viewed from the outside by an Englishman. Both serve to demonstrate that the salient characteristics of Welsh English as it was spoken 400 to 500 years ago are no longer necessarily recognizable in the Welsh English speech today.