Hypereutectic aluminium silicon alloys, e.g. casted AlSi17Cu4Mg, are commonly used in the automotive and aeronautical industries. These alloys consist of hard, abrasive silicon particles in a soft aluminium matrix and thus place high mechanical loads on the tool during machining processes. Polycrystalline Diamond or CVD (chemical vapour deposition) diamond based cutting tools can be used for the high speed machining of these alloys due to their high hardness and wear resistance. Diamond thin film coatings of different film morphologies are commonly applied on cemented carbide tools using Hot Filament CVD. The distinguishing characteristic to other coatings is utmost hardness resulting in high resistance to abrasion, low tendency to adhesion and low friction coefficient. The manufacturing of CVD diamond coated shaft type cutting tools is challenging due to the complex design of the cutting edges and the demanding stress behaviour during tool application. The influencing parameters of substrate type, chemical and mechanical substrate pre-treatment as well as diamond film modification on the tool cutting performance are discussed. The manufacturing route of CVD diamond coated thread milling drills is analysed with the use of material and tribological tests. The complex thread manufacturing tools are then applied in the machining of AlSi17Cu4Mg, whereby the tool performance is characterised with respect to their wear behaviour, the process forces and temperatures as well as the workpiece quality.