An information processing system comprising: a server; and a terminal of a first user and a terminal of a second user which are connected to the server via a network; wherein the terminal of the first user includes: a control section configured to generate first information using a detected result of an event based on sensor information indicating information related to the first user who plays golf, the first generated information including a playing image extracted from a captured moving image of the first user who plays golf on a basis of the detected result of the event, wherein to generate the first information, the sensor information and the moving image are synchronized, and the playing image comprises an image of a section in the moving image, out of the moving image, corresponding to a section based on a detected time point of the event in the sensor information; and a communication section configured to transmit the first generated information to the server; and wherein the server includes: a communication section configured to acquire the first generated information from the terminal of the first user; a transmission control section configured to control transmission of the first generated information to the terminal of the second user; and an acquisition section that acquires feedback information regarding the first generated information from the terminal of the second user for transmission to the terminal of the first user. a server; and a terminal of a first user and a terminal of a second user which are connected to the server via a network; wherein the terminal of the first user includes: a control section configured to generate first information using a detected result of an event based on sensor information indicating information related to the first user who plays golf, the first generated information including a playing image extracted from a captured moving image of the first user who plays golf on a basis of the detected result of the event, wherein to generate the first information, the sensor information and the moving image are synchronized, and the playing image comprises an image of a section in the moving image, out of the moving image, corresponding to a section based on a detected time point of the event in the sensor information; and a communication section configured to transmit the first generated information to the server; and wherein a control section configured to generate first information using a detected result of an event based on sensor information indicating information related to the first user who plays golf, the first generated information including a playing image extracted from a captured moving image of the first user who plays golf on a basis of the detected result of the event, wherein to generate the first information, the sensor information and the moving image are synchronized, and the playing image comprises an image of a section in the moving image, out of the moving image, corresponding to a section based on a detected time point of the event in the sensor information; and a communication section configured to transmit the first generated information to the server; and wherein the server includes: a communication section configured to acquire the first generated information from the terminal of the first user; a transmission control section configured to control transmission of the first generated information to the terminal of the second user; and a communication section configured to acquire the first generated information from the terminal of the first user; a transmission control section configured to control transmission of the first generated information to the terminal of the second user; and an acquisition section that acquires feedback information regarding the first generated information from the terminal of the second user for transmission to the terminal of the first user.