There is provided an image processing system including a first information processing apparatus and a second information processing apparatus. The first information processing apparatus performs processing, for a plurality of captured images simultaneously captured by a plurality of image capturing devices, for identifying a generation target image section for which a free-viewpoint image is generated, performs control to transmit image data for the generation target image section in each of the plurality of captured images as image data used for generation of a free-viewpoint image in the second information processing apparatus, and generates an output image including a free-viewpoint image received. The second information processing apparatus performs processing for acquiring image data for the generation target image section in each of the plurality of captured images, performs processing for generating a free-viewpoint image by using the image data acquired, and performs control to transmit the free-viewpoint image generated to the first information processing apparatus.