This chapter describes the evolution of key verbal constructions and markers from Old to Modern Chinese. First, the historical roots and the transformation of the resultative construction are examined, going back to the serial verb construction and the integration between the verb and the word for the action result [VR (verbal-result) integration], which is motivated by disyllabification. Historical changes in the system of negative markers are then discussed, focusing on the emergence of “méi (yǒu)” (没[有]) and “bù” (不). Second, the historical context for the emergence of the verb reduplication phenomenon is illustrated in detail for a better understanding of its forms and functions. In addition, this chapter argues that the boundedness of the predicate structure in Modern Chinese distinguishes it from Old Chinese. Finally, it is proposed that the main principle of the organization of sentence information in Modern Chinese is “accompanying feature + predicate center + result state”, offering historical reasons for its formation.