Rice fallow, a rainfed lowland agro-ecology, is presently gaining particular attention for sustainable cropping intensification in the South Asia. Nevertheless, cropping intensification of rice-fallow areas is largely challenged by non-availability of irrigation, the poor financial status of farmers and soil constraints. Indeed, fast depletion of the soil residual moisture remains the primary obstacle for growing a crop in succession in rice fallows. A field investigation was carried out to identify the most adaptable rice-winter crop rotation and to customize appropriate crop establishment practice for a winter crop that could conserve the soil moisture. Treatments comprised of three crop establishment practices for winter crops [utera (relay cropping, i.e. broadcasting of seeds in standing rice crop 15 days before harvesting), zero tillage (ZT) and ZT with mulching (ZTM)], and five post-rainy-season crops (lentil, chickpea, lathyrus, mustard and linseed). Results showed that lathyrus and lentil could be the potential winter crop in the rice-fallow condition of Eastern India. Except for mustard crop, the productivity of all the winter crops was higher in utera cropping, which was primarily attributed to early crop growth and higher soil moisture content over ZT and ZTM treatments. The higher water use efficiency was recorded under utera cropping over ZT and ZTM treatments. Higher system productivity (system rice equivalent yield) in rice-utera lathyrus (9.3 t ha) and rice-utera lentil (8.1 t ha) led to higher net returns and production efficiency over other treatments (winter crop × crop establishment practice). Benefits of rice residue mulching were prominent in lentil, mustard and linseed crop productivity. Energy use efficiency of different crop establishment practices follows the trend of utera > ZT > ZTM (p < 0.05), being highest in rice-utera lathyrus (5.3) followed by rice-utera lentil (4.8) crop rotations. The simulated data shows that winter crops grown under utera led to less emission of greenhouse gas (GHG) and low global warming potential (GWP) as compared to ZT and ZTM treatments. Rice-lathyrus, rice-lentil and rice-chickpea systems had lower NO emission than rice-mustard and rice-linseed rotations. Hence, lathyrus and lentil could be included in rice fallows ideally with utera for sustainable cropping intensification and improving the farmers' income in Eastern India.