High strength steel is similar to carbon steel in its composition. This material is developed originally for special uses such as aerospace and automobile due to its high strength and shock-free property in spite of lightness. But the chemical attraction of high strength steel is serious, which includes comminution of formation, metalization and strengthening. Machining results in built-up edge between this material and the tool. Especially the work hardening behavior results in tool life shortening, which was caused by temperature generation during machining. In this study, cooling system was made in which liquid nitrogen is supplied to circulate in order to make up for these weaknesses. Machining of high strength steels, which is recognized as difficult to machine materials, was conducted after tool is cooled at -195$circ$C. Experimental results showed that the tool was cooled down rapidly below -195$circ$C in about 200 seconds. The tool temperature of machining with cooling system was lowered by 60~95$circ$C than that of machining in room temperature. The hardness of the surface of chip is decreased by machining with cooling system. And the machining using the cooling system made it possible to increase shear angle, to retain smooth surface on chip without built-up-edge and to get a better roughness.