Introduction. The possibility of automated checking the works of participants of the Olympiads in programming is considered. The architecture and operation of the server part of the check system of performing the Olympiad programming tasks is described. Materials and Methods. The technologies of MySQL, PHP, C ++, JavaScript, HTML, and CSS are considered as the application framework. The test program is implemented in C ++ for operating systems of the Windows NT family. Research Results. The opportunity of the automated check of the Olympiad participants’ works in a real-time mode is fulfilled. A program-tester of the system is developed to check the programming Olympiad works. Discussion and Conclusions. As a result of the analysis of the global network and client/server technology operation, capabilities for the organization of interaction of the application with Internet-resources are defined. The developed application has proved expediency and efficiency of the interoperability of the application and Internet-resources.