Traditional agriculture in rainfed uplands of India has been experiencing low agricultural productivity as the lands suffer from poor soil fertility, susceptibility to water erosion and other external pressures of development and climate change. A shift toward more sustainable cropping systems such as conservation agriculture production systems (CAPSs) may help in maintaining soil quality as well as improving crop production and farmer’s net economic benefit. This research assessed the effects over 3 years (2011–2014) of reduced tillage, intercropping, and cover cropping practices customized for maize-based production systems in upland areas of Odisha, India. The study focused on crop yield, system productivity and profitability through maize equivalent yield and dominance analysis. Results showed that maize grain yield did not differ significantly over time or among CAPS treatments while cowpea yield was considered as an additional yield in intercropping systems. Mustard and horsegram grown in plots after maize cowpea intercropping recorded higher grain yields of 25 and 37%, respectively, as compared to those without intercropping. Overall, the full CAPS implementation, i.e., minimum tillage, maize–cowpea intercropping and mustard residue retention had significantly higher system productivity and net benefits than traditional farmer practices, i.e., conventional tillage, sole maize cropping, and no mustard residue retention. The dominance analysis demonstrated increasing benefits of combining conservation practices that exceeded thresholds for farmer adoption. Given the use of familiar crops and technologies and the magnitude of yield and income improvements, these types of CAPS should be acceptable and attractive for smallholder farmers in the area. This in turn should support a move toward sustainable intensification of crop production to meet future household income and nutritional needs.