A multiple viewpoint image capturing system includes: a plurality of cameras that capture videos in a predetermined space from different positions; a circumstance sensing unit that senses at least one of circumstances of the respective cameras and circumstances of the predetermined space, and outputs the sensed circumstances in a form of capturing circumstance information; and an event detector that detects a predetermined event based on the capturing circumstance information, determines whether to perform camera calibration in a case of detecting the predetermined event, and outputs camera calibration information that indicates the camera calibration to be performed in a case of determining that the camera calibration is to be performed.