Grinding of single crystal silicon may be achieved by two modes of material removal: ductile mode and brittle mode. Knowing of the brittle to ductile transition point at which the grinding process changes from the brittle mode to ductile mode is critically important for the realization of ductile mode grinding. This paper uses a new single grain diamond grinding method developed recently by the authors to investigate the brittle to ductile transition during grinding of single crystal silicon in all around. The results indicate that there exist four stages of brittle to ductile transition as the depth of cut is reduced: firstly, the surface cracks outside the grinding groove disappeared, secondlycracks on the bottom of the groove disappeared, then the lateral cracks ceased in the subsurface region, and finally the median crack is suppressed beneath the grooves. It is not until the depth of cut reaches the last transition point that a crack-free groove can be produced, therefore, the last transition stage is decisive. The critical depth of cut delineating the brittle to ductile transition point derived based on this criterion is 40 nanometers, which is much lower than that based on surface cracks.