High pressure is often generated locally on the contact surface of the machine elements. Since such high contact pressure may eventually cause the machine elements to break, the measurement of pressure distribution is important in the design situation. In this study, local high contact pressure occurred between a roller and a flat surface, such as rolling elements and inner/outer rings in a bearing, was measured by a pressure measurement method using a metal foil with microprojections. First, we prepared three types of electrodeposited nickel-phosphorous alloy foils with different projection densities and conducted calibration tests. Then the pressure distributions between the roller and the flat surface were measured and compared with Hertz’s formula. It was revealed that the experimental results are lower than Hertz’s formula because the true contact area is increases due to the contact of micro-projections even in the area where the roller and the flat surface are not in contact. Therefore, the pressure distributions were corrected by measuring the true contact area using a nickel-phosphorous alloy foils without micro-projections. The modified results show good agreement with Hertz’s formula. Finally, the contact pressure distribution between the crowned roller and the flat surface was measured by the proposed method, and it was confirmed that the maximum contact pressure of 1.6 GPa was occurred at the center of the roller.