Drilling operation with cryogenic assistance is beneficial in solving critical issues in machining difficult-to-cut materials and structures towards improving surface integrity, elongating tool life, and sustainable concerns etc., especially for high performance components in aerospace industries. This paper presents an overview of the state-of-the-art on this technique in recent years. It aims at analyzing its requirements and orient future directions. It starts with a summary with respect to its application on different categories of work materials, including metals, composites and hybrid stacks. Following the main methodologies from different aspects of modelling and experimental methods towards understanding the fundamentals are reviewed. The goal is to present a general idea of current approaches, discuss their advantages and disadvantages and orient the future directions of development. In addition, the impacts induced by this technique on cutting performance are reviewed in terms of cutting forces and temperatures, surface integrity, tool wear and sustainability. Finally, a brief summary is presented from different perspectives, and an outlook is recommended for future orientations.