To provide a delivery service that is convenient for customers and deliverers. A delivery service system comprising a sever 6 that can be connected to a plurality of customer terminals 8 and a plurality of deliverer terminals 10 over the internet 2, wherein information about a customer's desired pick-up/delivery date, time, etc., for a pick-up/delivery event, said information being input using the plurality of customer terminals 8 over the internet 2, is registered in databases 12, 14, 16 on the server 6 for each event. For new events registered in the databases, the server receives contract applications for events in which the area of the customer's address corresponds to a service area from deliverer terminals that have accessed the databases over the internet, registers the applications in the databases, and notifies the customer terminal associated with a new event for which applications are being received about the applications. The server receives notification of which of the deliverers that submitted applications has been approved over the internet from the customer terminal that received notification of the applications, and notifies the terminal of the approved deliverer of this fact, and the approved deliverer picks up/delivers the cargo associated with the new event.