The element wiþer is documented in Old English as a separate lexeme and a prefix. Altogether, Bosworth-Toller’s An Anglo-Saxon Dictionary records 69 wiþer-lexemes, which implies that wiþer- was relatively productive and flexible. Generally, wiþer- was added to words with the sense of ‘against’; in rare cases, it denoted ‘in return or compensation’ and ‘in the opposite direction’ (OED). Curiously, the majority of wiþer-lexemes are not recorded in Middle English: merely 24 words occur in MED. The aim of this study is to account for the loss of wiþer-lexemes. Potential causes are linguistic, such as low frequency and the similarity of the prefix wiþer- to wiþ-, and extra-linguistic, including competition with foreign items and changes in pragmatic associations of the words.