This report describes a two-dimensional monitoring system for milling machines using small-diameter tools. Small-diameter tools are used for high-speed milling, and they are indispensable for high-quality and high-productivity manufacturing. However, tool breakage occasionally occurs, and this becomes a serious problem in automated production. This study aims to develop a system for monitoring the cutting state that can prevent tool breakage. The proposed system consists of two charge-coupled device (CCD) cameras, an image processing device, a man-machine controller (MMC), and a machining center with an open computer numeric (CNC). This monitoring system is connected to the machining center by Ethernet. It enables the precise measurement of tool deflection during high-speed milling. In an experiment, we applied this system to the end milling of a steel plate under different cutting conditions, and we examined the relationship between tool deflection and the cutting conditions. In addition, we applied this monitoring system to measure tool wear, and we examined the relationship between tool deflection and tool wear. It was found that the proposed system enabled in-process monitoring of the cutting state and tool wear.