Temperature is one of the most influential factors in crop phenology and is projected to increase substantially due to climate change. To adapt to climate change, it is necessary to understand how crops develop depending on cultivar choice, sowing time, and growing environment under various warming conditions. To clarify the influence of these interactions, we investigated 216 combinations of the genotype × environment × management interaction of wheat (Triticum aestivum L.) development. These included nine scenarios of constant and seasonal warming conditions, two cultivar types (spring‐type and winter‐type wheat), six sowing dates, and two cultivation environments (relatively cool or warm area), and the change in wheat heading dates was simulated using sigmoid and exponential function–based models. Simulations of growing conditions 1−5 °C above the average temperature during 1981–2010 resulted in the faster growth of spring‐type cultivars, and the earlier the cultivars were sown, the faster they grew to heading stage. The winter‐type cultivars showed a smaller advancement to heading than the spring‐type cultivars, but the shortening period from sowing to heading became greater when grown in a cooler environment if the temperature significantly increased. In addition, increased temperatures in spring induced the advancement of heading more than similar conditions in winter. Our findings indicated that the advancement of the heading date varied greatly depending on the four‐factor combinations. Delaying sowing time and changing to winter‐type cultivars from spring‐type cultivars were thought to be effective adaptations; however, the adaptation strategies should be carefully planned depending on the agricultural management and warming conditions.