Winter wheat (Triticum aestivum L.) is the foundation of dryland cropping systems in the Central Great Plains. The objective of this study was to quantify the effects of four short‐season spring‐planted crops used to replace summer fallow on the subsequent winter wheat crop. Wheat was seeded into four crop stubbles [spring triticale (×Triticosecale Wittmack), dry pea (Pisum sativum L.), foxtail millet (Setaria italica L. Beauv.), and proso millet (Panicum miliaceum L.)] at sites near Akron, CO, and Sidney, NE, in the fall of 2004 and 2005. These summer fallow replacement crops were planted into silt loam soils at three different soil water levels at planting (low, medium, and high). Winter wheat water use was 3.6 cm greater, and grain yield was 662 kg ha−1 greater in the high water treatment compared with the low water treatment averaged across all sites and years. Winter wheat used an average of 4.3 cm more water following early planted summer crops (triticale and dry pea) than after late planted summer crops (foxtail and proso millet), but this increased water use did not consistently translate into increased grain yield as a result of terminal drought at Sidney in 2006. The high water treatment always had a positive net return. The high cost of pea seed ($3.30 kg−1, USD) strongly reduced profitability. The flexible summer fallow cropping system appears to be most applicable when using short‐duration summer annual forage crops such as triticale and foxtail millet.