The wide application of high pressure laminated (HPL) flooring has an insistent need for cutting tools with an excellent performance and fine cutting quality. Chemical vapor deposition (CVD) thick film diamond is a promising material for the machining of HPL flooring. In the present work, CVD thick film diamond tools were used to mill the wear resistance layer of HPL flooring. Wear volumes of flank face were examined by optical microscopy, and micro wear morphologies were observed by scanning electron microscopy (SEM). The experiments revealed that the predominant wear characteristics of CVD diamond tools were transgranular cleavage wear and intergranular peeling of the CVD diamond. Experimental results also showed that twin characteristic, cavity defect, micro crack and grain size of CVD thick film diamond contributed greatly to the wear process of CVD thick film diamond tools. The effects caused by the factors were also analyzed in detail in the paper.