Unfavorable weather conditions frequently cause farmers to plant maize (Zea mays L.) outside the optimum planting timeframe. We analyzed maize yield and phenology from a multilocation, year, hybrid relative maturity, and planting date experiment performed in Iowa, USA. Our objectives were to determine the optimum combination of planting date and relative maturity to maximize maize grain yield per environment and to elucidate the risk associated with the use of “full-season hybrids” when planting occurs beyond the optimum planting date. Analysis of variance (ANOVA) attributed 70% of the variability in grain yield to planting date and only 10% to relative maturity indicating that short and full-season hybrid relative maturities produced similar grain yields regardless of when they were planted as long as the crops reached maturity before harvesting. Our analysis indicated time to silking is a good indication of expected yield potential with a critical time (beyond which yield is reduced) to be 23 July for Iowa. Furthermore, we found that a minimum growing degree accumulation of 648°Cday during the grain-filling period maximized maize yield. Overall, this study brings new results to assist decision making regarding planting date by hybrid relative maturity across Iowa.