An information processing system includes a competition management system, a host terminal, a participant terminal, and a participant game device. The competition management system includes game competition generation means configured to generate information for holding a game competition, registration means configured to register participant information, pairing information generation means configured to generate pairing information indicating pairing of participants who play a communication game, and pairing information update means configured to update the pairing information based on report data. The competition management system generates a session for play of the communication game together by participants designated by the pairing information, in association with the designated participants.