This paper concerns an important and current problem of taking Corporate Social Responsibility (CSR) initiatives in the specific market conditions of the COVID-19 pandemic. CSR activities, aimed at combating COVID-19, contribute to creating favorable conditions for the sustainable development of enterprises and the entire society. In this work, analysis of the survey results, interviews with the initiatives’ beneficiaries, and brainstorm sessions with CSR specialists and companies’ employees allowed us to identify risk and opportunity categories, factors, and develop scales for their probability and consequences assessment. Survey results revealed that socially responsible actions are important in the fight against the coronavirus pandemic, and social expectations, in this regard, are growing. Two-parametric risk/opportunity matrix was used to calculate risk/opportunity level. The aim of this work is to present a new model of risk and opportunity assessment dedicated to organizations carrying out of CSR ventures in the pandemic era. The proposed risk and opportunity assessment model is an effective tool to identify the CSR initiative advantages and drawbacks, as well as a starting point for managing them, to maximize chances and minimize threats. Three examples of practical applications of the proposed model confirm that it can be successfully used in practice. The developed model is based on universal assumptions and criteria, so that it can be used in any country struggling with the pandemic.