While cutting metals is a well-studied problem, rock cutting due to its inherent complexity and more complicated physics due to its granular structure is less-known. The substantial role of the pore fluid pressure and confining pressure in the cutting process is one of these differences that may surface in practical engineering problems especially in deep subsurface drilling. Two sets of experiments were conducted in this research using single polycrystalline diamond compact (PDC) cutters. Regular scratch tests conducted in atmospheric pressure on Carthage Marble were compared with scratch/cutting tests performed under pressure. Finite element analysis (FEA) is then carried out to determine failure parameters by match lab measurement to investigate any potential changes in rock failure properties. It has been observed that pressurized conditions as low as 250 psi may convert the cutting process from intuitive fracture initiation and coalescence phenomenon to rock scooping. More ductile failure, formation of cutting ribbons and the size of cracks are some of these characteristics which are not observed in low confining pressures.