Provided is a content delivery system which includes an in-vehicle terminal and a content delivery server connected via wireless communication. The content delivery server includes a pre-sending unit which identifies a content that is likely to be used by the in-vehicle terminal in a dead spot where a communication status of the wireless communication is inferior, and sends the identified content to the in-vehicle terminal before a vehicle mounted with the in-vehicle terminal reaches the dead spot. The in-vehicle terminal includes an in-vehicle terminal storage unit which stores the content sent from the pre-sending unit.