Organic farming has positive, impact on environment, soil health, and healthy food quality. Worldwide demand for organic foods is increasing by leaps and bounds in recent years. The present investigation was undertaken during 2014 to 2018 to evaluate the effect of cowpea (Vigna unguiculata) co-culture with maize (Zea mays L.) on productivity enhancement over prevailing maize-fallow system, and to assess the feasibility of inclusion of short duration winter crops after maize with appropriate residue management practices on productivity and soil health. The experiment comprised of six cropping systems in main plot and three soil moisture conservation (SMC) measures options in sub plot. Results indicated that the inclusion of second crop in place of fallow and cowpea co-culture with maize increased average maize grain yield by 6.2 to 23.5% as compared to that of maize-fallow (MF). Use of maize stover mulch (MSM) + weed biomass mulch (WBM) increases maize grain yield by 19.1 and 6.5% over those of MSM and no mulch (NM), respectively. Various soil moisture conservation (SMC) measures had significant (p=0.05) effect on crop yields and water productivity. Double cropping system had significantly (p=0.05) higher amount of soil available NPK, soil organic carbon (SOC), microbial biomass carbon (MBC) and dehydrogenase activity (DHA) at 0-15 cm and at 15-30 cm depth than those under MF. The SWC measures of MSM+WBM had significantly higher available N, SOC, and MBC by 5.5, 4.8 and 8.1% than those under NM, respectively. Correspondingly, soils under MSM and MSM+WBM had 2.24 and 2.99% lower bulk density (ρb) in 0-15 cm and 2.21 and 2.94% lower ρb in 15-30 cm than that of NM. The energy use efficiency (EUE) was significantly higher under MCV (7.90%) over rest of the cropping sequences. MSM+WBM and MSM recorded 25.1 and 16.6% higher net energy over NM, respectively. The net return (INR 159.99×103/ha) and B:C ratio (2.86) were significantly higher with MCV system followed by MCR cropping sequence. MSM+WBM had significantly higher net return (INR 109.44×103/h), B:C ratio (2.46) over those under MSM (INR 97.6×103/h) and NM (INR 78.61×103/h). Overall the cowpea co-culture with maize and inclusion of short cycle winter crops along with MSM+WBM in maize-based cropping systems was found productive in terms of crop and water, profitable, energy efficient and sustained the soil health.