An example system includes a server and multiple information processing apparatuses. The server includes a competition request acceptance unit accepting a competition request from the information processing apparatus, and an opponent decision unit deciding an opponent of a user concerning the request accepted by the competition request acceptance unit. The information processing system includes a history storage unit storing competition history information for a user in a tournament, an exchange processing unit performing processing of exchanging at least a part of the competition history information between competing users, based on the decision made by the opponent decision unit, and a competition processing unit performing processing concerning a competition between the users. The opponent decision unit decides an opponent based on at least a part of competition history information stored in the history storage unit.