In colder agricultural regions like the upper Midwest, the availability of cold tolerant cover crop species is limited, which also limits double-cropping practices, especially in maize-soybean cropping systems. Although double-cropping can still be a viable option for some short-season grain crops, relay-cropping or intercropping can be a more suitable alternative in regions with short growing season. While the agronomic effects of cover crops in double or relay-cropped systems on nutrient management and soil fertility have been extensively examined in the literature, life cycle assessment (LCA) studies investigating the overall environmental impact of cover crops in cropping systems are still limited. The objective of this study was to assess and compare the environmental performance of a 2-year maize-soybean rotation without winter crops and with camelina, pennycress or rye as winter crops. The study provides a quantitative assessment of the environmental trade-offs of cropping sequences with or without cover crops, contributing to evaluate the overall sustainability of ecological intensification practices.