This chapter summarizes the causes and mechanisms of Chinese grammatical evolution. It discusses such factors as constraints of unidimensionality of time, pragmatic factors, analogy, reanalysis, and the basic word order SVO. It also examines the semantic and syntactic features of verbs and prepositions, as well as the morphological differences between them. The role of “yǒu” (有) in changing nouns into adjectives, and the pragmatic factors as motivation for the emergence of scalar meanings are also investigated. It highlights the grammatical similarities between Old Chinese and English while illustrating the impact of the basic word order of languages on morphology and syntax. Combining diachronic and synchronic perspectives, the author offers insights into two main mechanisms for grammatical evolution, reanalysis and analogy, and the restrictions on them. Internal evolution and language contact are also explored, highlighting the distinctions between Northwestern and Southeastern dialects of the Chinese language.