The article touches upon topical issues of the development of the Russian segment of the web services market in online environment in the global economic space. The study of the modern market of IT companies seems extremely relevant today. More and more firms need to start working in digital in order to expand business opportunities, optimize ways of interacting with customers, as well as increase competitiveness and economic efficiency indicators. The use of information technologies in business processes is becoming extremely necessary in the conditions of coronavirus restrictions, which increases the demand for IT companies’ services. In this regard, it is important to understand their basic strategies and assess their tendency to monopolize. “Previously, economists assumed that competitive markets for digital services are less prone to monopolization than markets for standard products. Now, monopolization, information asymmetry, and external (network) effects can be observed in digital markets” [1]. The purpose of the study is to identify the type of structure of the Russian segment of the web services market online in the global economic space and to assess the intensity of competition. To achieve this goal, the following tasks were solved: the relevant market was identified, its main characteristics and composition of participants were analyzed, the trends of its transformation in the conditions of COVID-19, the choice of criteria for analyzing the structure of the Russian market segment on the Upwork online exchange platform was justified. The results are based on an empirical study of statistical information on Novosibirsk companies operating on the Upwork platform. Such market parameters as a large number of firms, the insignificant height of barriers to entry into the industry, the predominance of non-price competition make it possible to identify it as a market of monopolistic competition. The article identifies the problems of antimonopoly regulation of the market of web services operating on digital platforms, namely: the complexity of their analysis and identification of the «relevant» market, the “blurring” of geographical and product boundaries, growing demand. The factors determining the competitive advantages of firms in the web services market and clients’ package, which, in turn, indirectly influence the choice of strategy, are systematized. The authors attempt to describe the motives of buyers’ behavior in the web services market when remotely selecting sellers in an online environment.