Wynnere and Wastoure is a debate poem of about 500 alliterative lines, which was written between 1352 and 1370 by an unknown poet, whose dialect indicates a North Midlands origin. Only one manuscript has been preserved and the end of the poem is missing.

In the poem the narrator relates a dream-vision in which he sees two armies lead by the allegorical figures of Winner and Waster. On the point of battle they are intercepted by a messenger and brought before the king, who can safely be identified as King Edward III. The king proposes to hear their case and pass judgement. During their subsequent debate Winner and Waster discuss the concepts of thrift and prodigality, touching on a wide range of topics concerning economy, religion, philosophy the concepts of thrift and prodigality, and politics. Finally, King Edward passes a highly ambiguous judgement and, without deciding the case in favour of one of the contestants, takes both Winner and Waster into his service.

Wynnere and Wastoure is to some extent a political poem of its day. In order to appreciate the political issue some socio-historical background is necessary. Under the financial burden of the Hundred Years War and the recurring Black Death, English society was changing. The gentry and lower nobility - represented by Waster - found themselves in financial difficulties and watched the rising of the merchant class - represented by Winner - to political and economical power with a jaundiced eye. King Edward III, renowned and notorious for being a spendthrift and a miser, understood how to use these social changes and frictions for his own ends.

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