The friction between cutting tools and the workpiece/chip can significantly affect tool wear, cutting force, cutting temperature, machined surface integrity, and machined parts' service performance. The friction and wear of cutting tools have long been a focus of researchers. In recent years, the development of new cutting methods and cutting tools, such as ultrasonic vibration-assisted cutting, cryogenic cutting, MQL cutting, and micro-textured tools, has changed the friction and wear rules of cutting tools. This Special Issue presents the latest advances in the fields of the friction and wear of cutting tools and cutting tool materials. This Special Issue contains 14 papers covering the design of anti-wear micro-textures/coatings, the development of new lubricating methods, cutting process modeling, and the analysis of friction mechanisms. We would like to sincerely thank all of the authors for submitting exceptional research papers to this Special Issue. We would also like to thank all of the reviewers who dedicated their precious time to carefully examine and help improve the quality of all of the submitted manuscripts. Finally, we would like to thank Ms. Faye Yin, Section Managing Editor, for her outstanding continuous support.