This paper presents a description of multiple sentence negation involving negative concord (NC) in the history of the English language with special emphasis given to the elimination of redundant Neg-elements, including cliticized adverbs, pronouns and adjectives. The type of redundancy manifested by the system of sentence negation within the suggested timeline is viewed as textually-bound, paradigmatic, and non-obligatory. The author of the paper outlines the distinctive features of the redundancy from a diachronic perspective. The study maintains that changes occurring in the English negation system represent the case of grammaticalization empirically observed in the data taken from literary monuments. The evolutionary path of the phenomenon in question is traced through three periods in the history of the English language, specifically Old English, Middle English and Early Modern English.