The continuous rice–wheat cropping system in South Asia has caused irreversible environmental damage, raising concerns about the long-term sustainability of the region’s agricultural systems. To address this issue, farm experiments were conducted for two successive years (2019–20 and 2020–21) to assess the impact of different cropping systems under conservation agriculture (CA) practices on the yield, productivity, and profitability of wheat. Results showed that the highest grain yield of wheat was observed in scenarios Sc6, Sc4, and Sc2, which involved full CA permanent-bed soybean (PB)–permanent-bed wheat (PB)–permanent-bed summer moong (PB), full CA permanent-bed maize (PB)–permanent-bed wheat (PB)–permanent-bed summer moong (PB), and partial CA puddled transplanted rice–Happy Seeder wheat–zero-till summer moong (ZT). Additionally, the highest irrigation water productivity (IWP), wheat grain macronutrient uptake, net return, and benefit–cost ratio (B:C ratio) were recorded under Sc6, full CA permanent-bed soybean (PB)–permanent-bed wheat (PB)–permanent-bed summer moong (PB) compared to farmers’ practice puddled transplanted rice (PTR)–conventional-till wheat–summer moong (Sc1) during both years. The system productivity also increased in scenarios Sc2, Sc4, and Sc6 (by 9.72%, 9.65%, and 14.14% in the first year and 10.68%, 14.14%, and 15.55% in the second year) compared to Sc1—farmers’ practice puddled transplanted rice (PTR)–conventional-till wheat–summer moong, Sc3—farmers’ practice fresh-bed maize (FB)–conventional-till wheat–summer moong, and Sc5–farmers’ practice fresh-bed soybean (FB)–conventional-till wheat (CT)–summer moong. The findings suggest that the conservation agriculture soybean–wheat–summer moong (Sc6) on permanent-bed cropping systems with inclusion legumes can be a potential option to enhance yield attributes, productivity, and profitability, as well as the sustainability of natural resources in the region while decreasing environmental footprints.