A coupled thermomechanical dynamic analysis is performed to simulate linear machining experiments effectuated by single diamond grains. Damage is described within a Johnson-Cook model. The damage parameters when machining Ti-6Al-4 V are optimized in a three dimensional model and a new concept of applying a damage limit when machining with negative rake angle is suggested. Here, a Fortran subroutine is written to calculate the damage field variable. The simulated cutting forces and temperature in the tool as well as the workpiece are validated. Validation experiments are carried out by single grain machining experiments at a depth of cut of 30 μm and at a linear cutting velocity of 0.8 m/s. Numerical challenges, such as chip separation criterion and settings of adaptive remeshing are addressed. Finally, it is shown that with an increase in the cutting edge radius, cutting forces and especially passive forces increase.