ABSTRACT This study examines how climate trends, soil moisture and phenological changes have influenced the magnitude and stability of Triticum aestivum L . production in the Kyiv region of Ukraine between 1968 and 2024. The purpose is to distinguish the impacts of warming, precipitation variability, soil moisture deficits and changes in growth stages (autumn cessation, spring regrowth, winter calm) on yield trends and interannual variability. Results show a statistically significant warming trend: annual temperatures rising ~0.050°C/year and during growing seasons ~0.046°C/year. Precipitation exhibits high interannual variability but no consistent long‐term trend; however, wet/dry extremes and moisture deficits during spring regrowth and summer are increasingly frequent. Soil moisture droughts at 50–100 cm depth, below a productive baseline (~112 mm), have become notably more common since 2007, especially in seasons with elevated temperatures. The winter calm period has steadily shortened and phenological variability during both autumn and spring growth has increased. Winter wheat yields have increased from ~4.6 to ~7.1 t ha −1 between early (1968–85) and recent (2015–24) decades, with an average linear gain of ~0.038 t ha −1 per year. However, interannual yield variability remains large and phenological timing (late autumn cessation and early spring regrowth) is strongly associated with higher yield in many years. Yield gains are driven largely by nonclimatic factors and yield stability is increasingly constrained by compound climatic stresses and phenological shifts. To sustain productivity under ongoing climate change, adaptation should emphasise phenology‐aware breeding, timing of sowing and spring renewal and soil moisture conservation during critical growth stages.