Global climate change increasingly impacts agroecosystems, particularly through high-temperature–drought and low-temperature–drought compound events. This study uses ground meteorological and remote sensing data and employs geostatistics, random forest models, and copula methods to analyze the spatial and temporal distribution of these events and their impact on winter wheat in the Huang-Huai-Hai Plain from 1982 to 2020. High-temperature–drought events increased in frequency and expanded from north to south, with about 40% of observation stations recording such events from 2001 to 2020. In contrast, low-temperature–drought events decreased in frequency, affecting up to 80% of stations, but with lower frequency than high-temperature–drought events. Sensitivity analyses show winter wheat is most responsive to maximum and minimum temperature changes, with significant correlations to drought and temperature extremes. Copula analysis indicates temperature extremes and drought severity are crucial in determining compound event probability and return periods. High-temperature–drought events are likely under high temperatures and mild drought, while low-temperature–drought events are more common under low temperatures and mild drought. These findings highlight the need for effective agricultural adaptation strategies to mitigate future climate change impacts.