This chapter discusses the relationship between conceptual structures and grammatical evolution from a perspective of cognitive linguistics, with a focus on verb conceptualization, conjunction development, progressive markers and future tense markers. It argues that the conceptualization differences between Old and Modern Chinese reveal an inverse relationship between the conceptualization complexity and the complexity of grammatical structures. It depicts the development of the main transitional conjunctions from restriction words in Chinese, as well as the lexical origins and the diversity of progressive aspect markers. The semantic basis for the emergence of future tense markers in Chinese is also illustrated, with reference to the English language. The author argues that future tense markers in English mainly come from verbs of intention (will, shall) and “go” verbs (be going to) while those in Chinese have a wide range of lexical origins.