Throughout my doctoral study I have encountered the problem of milling vulcanized rubber in a company specialized in the production of V-belts, which uses milling to generate the final surface of an assortment of V-belts. In this process I have encountered difficulties starting from fastening up to milling the rubber. At vulcanized rubber any error makes the workpiece to be rejected without the possibility to fix it, or not even to reuse the material. The reject rate at milling this assortment of V-belts is almost 40%. After we studied the literature from domain, we observed that the cutting issue of flexible polymeric materials is not well defined from some points of view, for this reason we made an experiment to observe the behavior of rubber at cryogenic and conventional milling, with a cutting speed of 2355m/min at a feed range between 0.0025 mm /tooth and 0.02 mm/tooth. As a result of the experimental study of milling vulcanized rubber type 3540, we observed that for the workpieces that were cooled with liquid nitrogen, the reject rate was reduced down to 20%. We also observed that, for the workpieces which were cooled with liquid nitrogen, feed milling had a small influence on the obtained surface quality.