Sentiment of risk affects the estimation of risk by investors and their decision making. However, in financial decision-making, increasing attention is being paid to the role of contextual information, which may provide more insight into managerial opinions and intentions, and has recently been used to more effectively predict a company's financial performance. The aim of the upcoming research is to investigate the simultaneous relationship between risk sentiment of annual reports and operational performance of 130 companies admitted to the Tehran Stock Exchange in the period from 2008 to 2021. For this purpose, the system of simultaneous equations was estimated using the two-stage regression method, and the risk sentiment of the annual reports was calculated using the content analysis method. The estimation results show the existence of a two-way relationship between the risk sentiment of annual reports with the asset return rate and the sales return rate, as well as the absence of a two-way relationship between the risk sentiment of annual reports and the equity return rate in companies listed on the Tehran Stock Exchange. Also, the relationship between the risk sentiment of annual reports with the rate of return on assets and the rate of return on equity relative to the influence of the management's interpretive report is significant. Keyword: Risk Sentiment, Operational Performance, Management's Interpretive Report, Annual Reports.