The ductile-to-brittle cutting mode transition in single grit diamond scribing of monocrystalline silicon is investigated in this paper. Specifically, the effects of scriber tip geometry, coefficient of friction, and external hydrostatic pressure on the critical depth of cut associated with ductile-to-brittle transition and crack generation are studied via an eXtended Finite Element Method (XFEM) based model, which is experimentally validated. Scribers with a large tip radius are shown to produce lower tensile stresses and a larger critical depth of cut compared with scribers with a sharp tip. Spherical tipped scribers are shown to generate only surface cracks, while sharp tipped scribers (conical, Berkovich and Vickers) are found to create large subsurface tensile stresses, which can lead to nucleation of subsurface median/lateral cracks. Lowering the friction coefficient tends to increase the critical depth of cut and hence the extent of ductile mode cutting. The results also show that larger critical depth of cut can be obtained under external hydrostatic pressure. This knowledge is expected to be useful in optimizing the design and application of the diamond coated wire employed in fixed abrasive diamond wire sawing of photovoltaic silicon wafers.