Risk analysis is one of the most important stages of risk management. The impact of uncertainty on achieving the target state of meso-economic systems target state is an issue that has not been sufficiently studied so far. The paper is dedicated to estimating the risks of implementation of the strategy for socio-economic development of Sevastopol, which may negatively or positively affect the degree and effectiveness of achieving the city’s strategic goals expressed by forecast values of such complex key indicator as the gross regional product (GRP). The following methods were applied in the study: comparative and statistical analysis, synthesis, expert evaluation, method of «bow-tie», SWOT-analysis, matrix of probability and impact, method of paired comparisons, scenario analysis. We have identified and classified the risks in implementing the strategy for socio-economic development of Sevastopol, compiling them into a risk map. Strengths (internal, positive risks) represent the realized competitive advantages of the city, while opportunities (external, positive risks) are, respectively, unrealized potential competitive advantages of Sevastopol. Thus, the main task of implementing the strategy for socio-economic development of Sevastopol from the standpoint of risk management is to maximize opportunities of the external environment, to implement the potential competitive advantages using the strengths of the city, while minimizing negative risks. It has been established that the lack of financial autonomy is the most significant factor affecting the rate of implementation of the city’s investment potential and the growth of the GRP. Additional study of this risk allowed to determine the list of preventive measures aimed at reducing the level of its negative impact on the implementation of Sevastopol’s development strategy. We have analyzed the scenarios of formation and implementation of the city’s tourist potential and assessed its impact on Sevastopol’s GRP. The study showed that negative risks that may have a high impact on the implementation of the strategy for socio-economic development of Sevastopol are mainly caused by the existing weaknesses of the city, which are concentrated in the key strategic projections: Finance, Production, Ecology. Growth points of Sevastopol are based on forming and achieving the industrial, transport and tourism potential while simultaneously developing the city’s intellectual, scientific and technological potential. On the whole, the presented results of the analysis can serve as a basis for risk response decision-making by city-management in order to improve the effectiveness and efficiency of the strategy for Sevastopol’s socio-economic development.