Machining is such a complex system that any foreseen result is practically impossible. However, research always helps to further understand the process, which contributes to providing positive results. Tool wear is always difficult to foresee, but it can be measured and related to several output parameters. In each individual application, there will be the best parameter that most reliably represents the tool wear. In the present investigation, the hole quality parameters (roughness and cylindricity), power consumption, electrical consumption of the machine tool and the acoustic emission signals were recorded and correlated to the tool condition in order to find the best output parameter for tool wear monitoring during the drilling of compact graphite cast irons. Two high-strength grades of compacted graphite cast irons (both CGI 500 with changes in the matrix and graphitic structure) were machined and compared to the standard grade (CGI 450) usually used in the manufacturing of engines using TiAlN-coated carbide drills at a constant cutting condition. The results showed that the best output parameter to monitor the tool wear was the electric current signal.