Artificial intelligence (AI) is becoming increasingly important, especially in the medical field. While AI has been used in medicine for some time, its growth in the last decade is remarkable. Specifically, machine learning (ML) and deep learning (DL) techniques in medicine have been increasingly adopted due to the growing abundance of health-related data, the improved suitability of such techniques for managing large datasets, and more computational power. ML and DL methodologies are fostering the development of new “intelligent” tools and expert systems to process data, to automatize human–machine interactions, and to deliver advanced predictive systems that are changing every aspect of the scientific research, industry, and society. The Italian scientific community was instrumental in advancing this research area. This article aims to conduct a comprehensive investigation of the ML and DL methodologies and applications used in medicine by the Italian research community in the last five years. To this end, we selected all the papers published in the last five years with at least one of the authors affiliated to an Italian institution that in the title, in the abstract, or in the keywords present the terms “machine learning” or “deep learning” and reference a medical area. We focused our research on journal papers under the hypothesis that Italian researchers prefer to present novel but well-established research in scientific journals. We then analyzed the selected papers considering different dimensions, including the medical topic, the type of data, the pre-processing methods, the learning methods, and the evaluation methods. As a final outcome, a comprehensive overview of the Italian research landscape is given, highlighting how the community has increasingly worked on a very heterogeneous range of medical problems.