High-speed cutting is one of the key issues in mould manufacturing. But to apply high-speed milling to mould manufacturing, unlike conventional milling, it is necessary to define specific cutting parameters. This article aims to define the influence of milling strategies and cutting parameters, such as cutting speed, feeding speed, cutting tool tilting angle, on the process stability. Long tool life and cutting strategy have a major influence on the results of machining hardened steel. Machining with drawing cut and down-cutting in copper and with drawing cut and up-cutting in hardened steel gave the best results with respect to tool wear and surface quality. Tool approach across the feeding direction results in heavy impact loads on the tool which lead to heavy tool wear and substantial dimensional deviations. Good surface quality is achieved in machining of a work piece of 2 363 steel (X100CrMoV51) hardened to 60 HRC, using the strategy of up-cutting with drawing cut and a tool approach with a tilting angle of 15 degrees. While up-cutting allows for achieving better surface quality, down-cutting provides longer tool life than up-cutting for all angles of approach.