A calendar selling system comprises a server that stores information of a plurality of pictures and a terminal that receives information of the plurality of pictures from the server and shows the information to a user, and the user selects pictures for a calendar from the plurality of pictures according to the information with the terminal to order the calendar. The calendar selling system also comprises a printing office that receives information of the pictures selected by the user from the server, prints the calendar with the pictures selected by the user and dates set by the user or automatically set according to the date of the order, delivers the calendar to the user and bills the user. Therefore, the desired calendar can be purchased all through the year and delivered to the user quickly.