Crop rotation, a sustainable agricultural technique, has been at humanity’s disposal since time immemorial and is practised globally. Switching between cover crops and cash crops helps avoid the adverse effects of intensive farming. Determining the optimum cash-cover rotation schedule for maximizing yield has been tackled on multiple fronts by agricultural scientists, economists, biologists and computer scientists, to name a few. However, considering the uncertainty due to diseases, pests, droughts, floods and impending effects of climate change is essential when designing rotation strategies. Analysing this time-tested technique of crop rotations with a new lens of Parrondo’s paradox allows us to optimally use the rotation technique in synchrony with uncertainty. While previous approaches are reactive to the diversity of crop types and environmental uncertainties, we make use of the said uncertainties to enhance crop rotation schedules. We calculate optimum switching probabilities in a randomized cropping sequence and suggest optimum deterministic sequences and judicious use of fertilizers. Our methods demonstrate strategies to enhance crop yield and the eventual profit margins for farmers. Conforming to translational biology, we extend Parrondo’s paradox, where two losing situations can be combined eventually into a winning scenario, to agriculture.