A method based on extensive laboratory and field measurements was developed to determine the dependence of specific rock cutting energy (SEc) on specific drilling energy (SEd) for machines with different operating and design characteristics and similar breaking mechanics. Laboratory measurements were performed on a linear rock cutting device and a laboratory drill, using a measurement system to measure electrical power and cutting forces using force/torque transducers. Field power consumption measurements were performed on a chainsaw cutting machine and a hydraulic rotary drill under real working conditions in the dimension stone quarries. The analysis of the measured results confirmed the strong dependence of the specific rock cutting energy on the specific drilling energy and confirmed that laboratory devices can be used to simulate actual rock cutting and drilling process. In addition, the results are applicable in the dimension stone exploration and exploitation phase in order to assess and reduce energy consumption by optimizing the operating parameters of the chain cutter and/or the hydraulic rotary drill.