Monitoring biotic and abiotic stress in agricultural crops is important for sustainable food and agriculture. Nanotechnology provides emerging opportunities for plants to boost stress tolerance, wherein chiral nanomaterials have been developed and studied for their intrinsic chirality or spatial asymmetry at the nanoscale. Chiral nanomaterials have been proposed for a wide range of uses, including the development of biosensors, the production of targeted antiviral and antibacterial agents, and the preparation of superior fertilizers, showing the potential to achieve higher yields and improved quality of crops. Chiral-dependent performances are related to the biorecognition of enantiomers, wherein the response to different isomers primarily originates from differences in their physical structure. A phenomenon can be exploited to develop new monitoring approaches and targeted therapy to alleviate biotic and abiotic stress that affects crop quality and quantity, showing enantiomer-dependent interactions between chiral nanomaterials and biological molecules in plants. Taken together, nanoscale chirality provides new opportunities that should be further explored to improve plant protection and nutrition and to support more sustainable food production systems.