Growers are interested in crops that can be used as alternatives to complement winter wheat grown as a monocrop. The objective of this study was to compare agronomic performance and net return of winter wheat and soybean cropping systems under rainfed environments. Cropping systems of monocrop winter wheat (Triticum aestivum L.), monocrop soybean [Glycine max (L.) Merr.], and 3‐crop/2‐year (early‐season soybean, winter wheat, and doublecrop soybean in a biennial rotation) were evaluated at Lahoma, OK. Over three years, early‐season and monocrop soybean yields averaged 35 and 31 bu/acre, respectively, but were not significantly different in any year. Doublecrop soybean averaged 13 bu/acre following wheat. Reduced yields for doublecrop soybean were attributed primarily to highly variable rainfall amount and distribution during growing seasons. Wheat yields were similar for monocrop and 3‐crop/2‐year systems, averaging 54 and 53 bu/acre, respectively. Crop production reflected the rainfall variability occurring in such a production environment. Enterprise budgeting was used to determine revenues, costs, and net returns for cropping systems. Annualized average net returns to land, labor, and management were $59/acre for monocrop soybean, $52/acre for monocrop winter wheat, and $77/acre for 3‐crop/2‐year. The results can be used as a tool to determine cropping systems to use in managing crop production.