Accurate mapping of winter wheat over a large area is of great significance for guiding policy formulation related to food security, farmland management, and the international food trade. Due to the complex phenological features of winter wheat, the cloud contamination in time-series imagery, and the influence of the soil/snow background on vegetation indices, there remains no effective method for mapping winter wheat at a medium spatial resolution (10–30 m). In this study, we proposed a novel method called phenology-time weighted dynamic time warping (PT-DTW) for identifying winter wheat based on Sentinel 2A/B time-series data. The main advantages of PT-DTW include (1) the use of phenological features in two periods, i.e., the greenness increase before winter and greenness decrease after heading, which are common to all winter wheat and are distinct from the features of other land cover types, and (2) the use of the normalized differential phenology index (NDPI) instead of traditional vegetation indices to provide more robust vegetation information and to suppress the adverse impacts of soil and snow cover, especially during the before-winter growth period. The proposed PT-DTW method was employed for winter wheat mapping based on Sentinel 2A/B data on the Huang-Huai Plain, China. Validation with visually interpreted samples showed that the produced winter wheat map achieved an overall classification accuracy of 89.98% and a kappa coefficient of 0.7978, outperforming previous winter wheat classification methods. Moreover, the planting area derived from PT-DTW agreed well with census data at the municipal level, with a coefficient of determination of 0.8638, indicating that the winter wheat map produced at 20 m resolution was reliable overall. Therefore, the PT-DTW method is recommended for winter wheat mapping over large areas.