Drilling is one of the most important operations in machining industry and usually the most efficient and economical method of cutting a hole in metal. From automobile parts to aircraft components, almost every manufactured product requires that holes are to be drilled for the purpose of assembly, creation of fluid passages, and so on. It is therefore desirable to monitor drill wear and hole quality changes during the hole drilling process. One important aspect in controlling the drilling process is monitoring drill wear status. A drill-wear monitoring system provides information about drill status. With the information, optimum planning for tool change is possible. And drill-wear monitoring system in needed to evaluated drilled hole quality and the wear of drill. Accordingly, this paper deals with an on-line drill wear monitoring system of the detection of tool wear with the computer vision and the area of the drill flank wear is analyzed quantitatively by the system.