This article reviews and analyzes the approaches utilized for monitoring cutting tool conditions. The Research focuses on publications from 2012 to 2022 (10 years), in which Machine Learning and other statistical processes are used to determine the quality, condition, wear, and remaining useful life (RUL) of shearing tools. The paper quantifies the typical signals utilized by researchers and scientists (vibration of the cutting tool and workpiece, the tool cutting force, and the tool’s temperature, for example). These signals are sensitive to changes in the workpiece quality condition; therefore, they are used as a proxy of the tool degradation and the quality of the product. The selection of signals to analyze the workpiece quality and the tool wear level is still in development; however, the article shows the main signals used over the years and their correlation with the cutting tool condition. These signals can be taken directly from the cutting tool or the workpiece, the choice varies, and both have shown promising results. In parallel, the Research presents, analyzes, and quantifies some of the most utilized statistical techniques that serve as filters to cleanse the collected data before the prediction and classification phase. These methods and techniques also extract relevant and wear-sensitive information from the collected signals, easing the classifiers’ work by numerically changing alongside the tool wear and the product quality.