Anthropogenic activities have impacted land management in the Midwest by transforming perennial grasslands and savannas into annual croplands. Agriculturalists presently have a considerable impact on the ecological balance of expansive amounts of land. This study investigates soil water and root dynamics under six different annual and perennial vegetative cover types. Measurement of growing season surface soil moisture showed no significant differences between annual compared to perennial sites. Depth of water uptake determination indicated that buckbrush and oak acquired moisture from deeper depths (5-10 cm to groundwater) than corn and soybean (5-10 to 10-20 cm). Depth of water uptake for sedge, brome grass, and big bluestem were comparable (0-5 to 10-20 cm) to corn and soybean. Despite distinct above ground appearances vegetative cover types may retain below ground similarities far beyond initial restoration. These considerations emphasize the expediency with which elements of healthy agroecosystems must continue to be distinguished and implemented.