Numerous studies have reported phenological changes and their driving mechanisms in spring flowering plants. However, there is little research on the shifts of winter flowering phenology and its response to forcing and chilling requirements. Based on the China Phenological Observation Network (CPON) ground observation data from nine sites over the past 20 years, we explored the spatial and temporal variation patterns of flowering plants and their response to chilling and forcing in wintersweet (Chimonanthus praecox L.), a common winter flowering plant species in temperate and subtropical zones of China. We used three chilling models (chilling hour, Utah, and dynamic models) and the growing degree hours (GDHs) model to calculate each site’s daily chilling and forcing. Using the partial least squares (PLSs) regression approach, we established the relationship between the first flowering date (FFD) and pre-season chilling and forcing in wintersweet, based on which we identified chilling and forcing periods and calculated chilling and forcing requirements. This study found that the FFD of wintersweet in China showed an overall advancement trend during the last 20 years. Still, there were temporal and spatial differences in the FFD of wintersweet among different sites. The PLS results showed that wintersweet also had periods of chilling and forcing, both of which co-regulated wintersweet flowering. We found the forcing and chilling requirements of wintersweet varied significantly from site to site. The higher the latitude is, the more chilling requirements are needed. The chilling requirements for wintersweet were about 6.9–34.9 Chill Portions (CPs) and 1.4–21.6 CP in the temperate and subtropical zones, respectively, with corresponding forcing requirements of 3.2–1922.9 GDH and 965.3–8482.6 GDH, respectively. In addition, we found that the temperature requirements of wintersweet were correlated by a negative exponential relationship, suggesting that chilling and forcing requirements have an antagonistic effect on initiating flowering phenology. Our results could help us understand how flowering dates of winter flowering plants respond to climate change.