This article presents the characteristics of delamination wear on the clearance face of newly coated K10 cutting tools when milling particleboard. The K10 cutting tools were multilayer coated with titanium aluminum nitride (TiAlN)/titanium silicon nitride (TiSiN), TiAlN/titanium boron nitride (TiBN), and TiAlN/chromium aluminum nitride (CrAlN). Particleboard with a density of 0.61 g/cm³ was cut using the multilayer-coated tools and a monolayer-coated (TiAlN) tool. Cutting tests were performed at a high cutting speed of 41.8 m/s and a feed rate of 0.2 mm/rev to investigate the delamination wear on the clearance face of these coated tools. Experimental results showed that the newly multilayer-coated tools experienced a smaller amount of delamination wear than the monolayer-coated tool when milling the particleboard. The best multilayer coating was TiAlN/CrAlN; that tool only suffered a slight chipping on the cutting edge at a cutting length of 1 km. The high hardness, low coefficient of friction, high resistance to oxidation, and high resistance to delamination wear of the multilayer-coated TiAlN/CrAlN tool indicate a very promising applicability of this coating for high-speed cutting of abrasive wood-based materials.