This paper discusses the evolutionary path of sentence negation development in the history of the German language. The peculiarities of means of multiple negation realization in the studied periods of the language development have been analyzed, taking into account changes in the paradigm of negative markers of Old, Middle, and Early New High German. In terms of polynegation, the attention has been focused on the negative concord, accompanied by a preverbal marker and an additional negative adverb or pronoun. It has been found that the implementation of the negative concord involves a single semantic core of negation. The reasons for the transition from double to single negation in the appropriate period of the German language development have been highlighted. The study of the mechanisms of grammaticalization made it possible to trace the development of negative grammatical constructions, namely the loss of syntactic independence and morphological diversity of elements in the syntactic paradigm. The gradual nature of sentence negation has been presented according to Jespersen's cycle, which reflects the weakening of the mononegative proclitic with its subsequent strengthening with the help of an additional negative pronoun, and, as a result, the return to the mononegative model in which the second negative element was implemented. A particular attention has been paid to the phenomenon of grammatical redundancy and its manifestations in the transformation of the negative model in diachrony. In linguistic studies, grammatical redundancy is characterized as a property or language behavior when the same function is realized by two or more means. The gradual elimination of the additional negative element contributed to the isolation of the mononegative model inherited by Modern German. It has been also shown that structural changes in negative sentences are closely related to a relatively free or limited word order.