In the eastern Great Plains, winter wheat (Triticum aestivum L.) and different soybean [Glycine max(L.) Merr.] maturity groups (MG) are grown in various cropping systems to diversify crop production. A 10‐year field study was conducted in southeastern Kansas to evaluate effects of multi‐cropping systems on grain yield and net economic returns. Cropping systems evaluated were: (i) annual double‐cropping of wheat and soybean (MG IV); (ii) four 2‐year rotations of wheat‐soybean double‐cropped followed by full‐season soybean the next year, where the same soybean MG (I, III, IV, and V) was grown both years; and (iii) a 3‐year rotation of wheat, wheat, and full‐season (MG V) soybean. On average, wheat yields ranged from 51 bu/acre following early MG I soybean in the 2‐year double‐crop rotation to 36 bu/acre following MG IV soybean in the annual double‐cropping system. Wheat yield differences were primarily determined by planting date. Full‐season (MG V) soybean yields were highest (35 bu/acre) following two years of wheat in the 3‐year rotation. Double‐crop soybean yields in the annual double‐cropping system averaged 26 bu/acre for MG IV. Full‐season and double‐crop soybean yields in the 2‐year double‐crop rotation system were significantly greater for traditional MGs (III, IV, and V) than MG I. Net economic returns averaged $101/acre for annual double‐cropping, which was $10 to $25/acre higher than 2‐year systems with MGs III, IV, and V; whereas, net returns were lowest for the 3‐year rotation ($51/acre) and for the 2‐year system with MG I soybean ($44/acre).