Drilling operation with cryogenic assistance is beneficial toward solving critical issues in machining difficult-to-cut materials and structures, especially in terms of improving surface integrity, elongating tool life, sustainability, and so on for providing high-performance components in aerospace industries. This article 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 concerning its application for different categories of work materials, including metals, composites, and hybrid stacks. Then, the main methodologies of numerical modeling and experimental characterization toward understanding the fundamentals are reviewed. The goal is to present a general view of current approaches, discuss their advantages, and disadvantages to understand the requirements toward future work. In addition, impacts of cryogenic drilling on cutting performance are reviewed in terms of thermomechanical loadings, surface integrity, tool wear, and sustainability. Finally, a brief summary is presented from different perspectives, and an outlook is recommended for future orientations.