Rotating crops is a sustainable agricultural technique that has been at the disposal of humanity since time immemorial. Switching between cover crops and cash crops allows the fields avoids overexploitation due to intensive farming. How often the respite is to be provided and what is the optimum cash cover rotation in terms of maximising yield schedule is a long-standing question tackled on multiple fronts by agricultural scientists, economists, biologists and computer scientists, to name a few. Dealing with the uncertainty in the field due to diseases, pests, droughts, floods, and impending effects of climate change, is important to consider when designing the cropping strategy. Analysing this time-tested technique of crop rotations with a new lens of Parrondo's paradox allows us to improve upon the technique and use it in synchronisation with the burning questions of contemporary times. By calculating optimum switching probabilities in a randomised cropping sequence, suggesting the optimum deterministic sequences and judicious use of fertilisers, we propose methods for improving crop yield and the eventual profit margins for farmers. Overall we also extend the domain of applicability of the seemingly unintuitive paradox by Parrondo, where two losing situations can be combined eventually into a winning scenario.