Heat transfer phenomena at the rock–cutter interface are extremely significant since they affect the polycrystalline diamond compact (PDC) cutter's performance in rock cutting/drilling processes. The understanding of how temperature and heat flux responses in the cutter influence the intrinsic mechanisms of the rock–cutter interactions is an essential prerequisite for providing insights to enhance the performance of PDC cutters and to optimize rock cutting/drilling processes. In this paper, a mixed boundary value heat transfer problem was formulated to analytically describe the heat transfer phenomena in the PDC cutters during two-dimensional (2D) orthogonal rock cutting under steady state conditions. An analytical solution in the form of an infinite series was derived based on the method of separation of variables, the use of appropriate simplifications in the formulated problem and the separation of the thermal from the mechanical phenomena. A series of experimental tests were conducted on a newly developed rock cutting testbed to calibrate the process parameters in the analytical solution and then to confirm the validity of the assumed boundary conditions. The comparison between the newly derived analytical solution and the experimental data shows a good match in terms of temperature responses during rock cutting performed by PDC cutters.