Plastic film mulching often increases the yield of winter wheat in the Loess Plateau of China, but the physiological mechanisms are unclear, especially in response to the interaction between mulch and water supply. In this study, we investigated the interactive effects of initial soil water (dry, moderate, and wet), soil cover (plastic mulch, bare soil), and seasonal conditions on the dynamics of dry matter partitioning, water-soluble carbohydrates (WSC), and flag leaf senescence, and their relations with yield and its components. Plastic mulch increased dry matter accumulation at anthesis and maturity relative to bare soil, with no interaction with season or initial soil water. Allocation of dry matter to leaf, stem, and spike did not change with soil cover. Compared with bare soil, mulch increased WSC accumulation by 14% at anthesis and its translocation by 16%. Soil cover did not influence the senescence of flag leaf after anthesis as indicated by similar dynamics of the C:N ratio. Grain yield was higher under plastic mulch than bare soil in two out of three seasons, and was associated with a higher translocation amount of WSC and post-anthesis dry matter that linked grain weight, grain number, and harvest index.