This paper investigates the cultural encounters between China and the West during the late Ming dynasty through the case of Matteo Ricci, one of the most influential Jesuit missionaries in China. It asks how Ricci’s strategies of cultural adaptation—such as mastering the Chinese language, adopting Confucian attire, and reconciling Christian theology with Confucian thought—enabled him to function as both a mediator and a challenger within Sino-Western exchanges. Drawing on Ricci’s Chinese Notebooks and contemporary scholarship, the study analyses his role in transmitting Western science and philosophy to China while simultaneously reshaping Confucian traditions and influencing European perceptions of Chinese culture. It argues that Ricci’s experience exemplifies not merely religious proselytisation, but a broader process of cultural negotiation marked by dialogue, appropriation, and conflict. By situating Ricci within the wider framework of late Ming intellectual and social history, the paper highlights his contribution to the emergence of early modern cross-cultural knowledge production, offering insights into the dynamics of intercultural communication still relevant in global contexts today.