Northeast China (NEC) is a region sensitive to climate change. However, the adoption of long-season maize cultivars in NEC has caused a substantial yield increase under climate change conditions. It is important to determine whether such cultivar adoptions are effective throughout the whole NEC to sustainably increase grain yield. In this study, phenological observations and meteorological data at six sites from 1981 to 2018 were used to detect thermal time (TT) trends during the maize growing period. TT, as a parameter for measuring changes in maize cultivars, was used in the crop simulation model CERES-Maize to examine the variations in maize yield produced with different cultivar × climate combinations in different decades. In NEC, both TTs from emergence to anthesis and from anthesis to physiological maturity showed significant increasing trends from 1981 to 2018. Simulation results for humid areas revealed that adopting longer-season cultivars during 2000–2018 caused yield increases, ranging from 6.3% to 13.3%, compared with the 1980s. However, for stations in semi-humid areas, maize grain yield showed a decrease or a small increase (from −12.7% to 8.0%) when longer-season cultivars were adopted during 2000–2018. For semi-humid areas, decreasing trends in the ratios of rainfed yield to no water-stress yield (Yrainfed/Yno water-stress) and lower Yrainfed/Yno water-stress values during 2000–2018 indicated a growing sensitivity of maize production to water, which was attributed to changes in TT and precipitation. Our results indicate that, for the semi-humid area, maize yield was limited by water after introducing cultivars with higher TT requirement under climate change conditions. Therefore, securing food supplies will depend on increases in water-use efficiency levels and other adaptive strategies, such as varietal diversification, drought-resistant varieties, conservation tillage and irrigation.