A new contact-type on-machine measurement system is designed and developed for the evaluation of a micro cutting edge profile. The measurement system is composed of a compact probe unit having a sharp stylus mounted on a flexible beam, an inner displacement sensor for the detection of the stylus displacement, and a two-axis precision positioning system. For the evaluation of tool faces having a steep slope, a new probing procedure with the enhancement of the inner displacement sensor integrated into the probe unit is newly proposed. After the design and development of the probe unit, the feasibilities of the developed measurement system and the proposed probing procedure are demonstrated through some basic experiments. Regarding the out-of-straightness and angular error motion of the two-axis positioning system employed in the developed measurement system, a pair of length gauges is newly employed to reduce the influences of error motions of the stage system. The topographic profile of the micro cutting edge obtained by the measurement system with the modified probe unit is then compared with those obtained by a commercial stylus profiler and a laser confocal microscope. The feasibility and effectiveness of the developed on-machine tool edge profile measurement system are also demonstrated through uncertainty analysis based on the GUM with the Monte-Carlo method.