Water resource management is pivotal for sustainable operations, particularly in agriculture, as, for example, the sector accounts for about 70% of the global freshwater exploitation. Specifically, in countries like India, the prevalence of water-intensive cropping systems such as ‘rice – wheat’ in tandem with traditional irrigation methods such as flood irrigation has resulted in alarming water scarcity levels and marginal economic returns. Multiple cropping systems, i.e., cultivating several crops in a growing season over the same land, can offer additional revenue opportunities but would lead to further decline in the water table, currently falling by 0.54 m per year in Punjab, the ‘Breadbasket of India’. Furthermore, smallholder farmers' return-on-investment remains challenged with consequent significant financial and social stress reported. Therefore, it is necessary to generate robust evidence to inform farmers' decision-making process to adopt multiple cropping systems. Multiple cropping systems can help ensure the environmental and economic sustainability of agricultural operations, which, possibly facilitated by precision irrigation, can ultimately improve the livelihood of farmers. In this regard, this research aims to propel the sustainable transition in Indian agriculture via generating real-world evidence that evaluates the environmental and financial viability of multiple cropping systems in Punjab, enabled by subsurface drip irrigation and fertigation techniques. Specifically, yield attributes, water balance, nutrient leaching, water productivity, net returns and benefit-cost ratio are assessed for the ‘summer mungbean – maize – wheat’ system, based on primary data from two growing seasons. The study findings demonstrate that subsurface drip irrigation and fertigation techniques could lead to circa 30% savings in irrigation water due to low drainage losses. In addition, a corresponding increase in farmers' net returns can be achieved compared to the conventionally used flood irrigation method in the ‘summer mungbean – maize – wheat’ cropping system.