This study, for the first time, investigates the physical association between Predecessor Rain Events (PREs) and peak runoff generation in seven catchments over the Upper Mahanadi River basin (UMRB), India. A statistical–dynamical framework is developed to assess the compounding impact of PREs (as preconditioned events) versus riverine floods during both retrospective and projected climate. Based on models' fidelity to capture historical climatology, we select four out of nine Global Climate Models (GCMs) during historical (1980–2005), and the three projected time windows, that is, near future (2010–2039), mid‐century (2040–2069), and the far future (2070–2099) planning horizons with RCP8.5 emission scenario. We assess changes in compound flood hazards in historical versus projected periods using a newly proposed Bivariate Hazard Ratio (BHR) index, which represents the ratio between bivariate return periods during the projected versus the historical time windows. Assessing bivariate return periods (characterized by ‘AND’ operator) of rainfall‐driven compound floods shows decreased flood hazard in the mid‐century and far‐future planning horizons. Accounting ranges of uncertainty from climate model simulations and the propagation of uncertainty across the numerical model chain, overall we show considering PRE as the covariate, floods in larger catchments show an increase in compound flood hazard in the projected period.