A holistic approach in the design of cropping systems is essential to boost productivity in a sustainable manner. One of the most important decisions in the cropping system is the way that crops are organized in sequences, which is commonly oriented to obtain high yields and associated economic return while minimizing variability and risk. Increased cropping intensity based on sequenced winter/summer crops has proven to raise annual land productivity due to a larger utilization of environmental resources. In this study, we aim to compare a soybean monoculture sequence with more diverse and intensified crop rotations in terms of resource use, overall productivity, and economic return in four sites, along six years, exploring a relatively wide range of environmental conditions in the central area of the Argentine Pampas. Results showed that more intensified and diverse cropping sequences yielded 41–51% more, in average, than soybean monoculture, given that this latter crop makes use of available environmental resources only during summer. In addition, despite higher production cost when growing more diverse and intensified rotations, annual gross margin was 10–13% higher, in average, than soybean monoculture. According to our results, cropland intensification resulted in larger productive, economic, and environmental benefits. At this point, new alternative winter crops and intensified cropping systems may expand. However, to effectively promote such process in the Pampas, it appears that policy decision makers should target the development of new markets and create opportunities to use or sell the extra production.