The interplay between internationalization and digitalization (IDI) is a relatively young research domain that is finding its way into numerous academic journals, which motivates us to systematically portray the proceedings and evolutions of this interplay over time, analyze its methodological and theoretical background and, more importantly, provide insights to guide future research on these phenomena. Combining qualitative and quantitative approaches, we analyze 68 peer-reviewed international business and management papers to explore the structure of knowledge production and identify the emerging trends. Our research reveals four key stages of the debate: (a) how IDI influences interorganizational aspects (1996–2004), (b) how digitalization influences the balance between perceived risk and returns in internationalization (2005–2009), (c) how digital advances and available internationalization channel alternatives influence IDI (2010–2014), and (d) how IDI influences intraorganizational aspects (2015–2019). Moreover, our analysis reveals heterogeneity across theoretical perspectives, methods, and research themes over the years. Finally, we identify theoretical and methodological challenges related to IDI research.