In India, agricultural intensification and technological specialisation have led to the prevalence of monoculture. Diversity within crop species has been gradually declining since the advent of the Green Revolution in the 1960s. Increasingly frequent weather shocks induce agrarian stress, thus creating a need for robust adaptation responses. Using district-level agricultural data for the period between 1966 and 2015, this article aims to assess whether crop diversification can cushion yield losses due to droughts. The results of this study indicate that diversification enhanced resilience against droughts during the Green Revolution period. However, post-Green Revolution, specialisation seems to have helped mitigate the adverse effects of rainfall deficit. In the absence of weather extremes, monoculture is found to be more lucrative due to both supply- and demand-side factors such as improved inputs, irrigation and infrastructure facilities, government’s support prices and consumption demand patterns. Crop diversification is identified as a potential adaptation strategy against certain types of weather extremes. However, in some cases, crop diversification alone is inadequate in enhancing the drought resilience of the cropping system in India. To ensure drought resilience, combining crop diversification with other measures such as enhancing irrigation and agricultural diversification needs to be considered.