Spatiotemporally mapping winter wheat is imperative for informing and shaping global food security policies. Traditional mapping methods heavily rely on sufficient and reliable samples obtained through labor-intensive fieldwork and manual sample collection. However, these methods are time-consuming, costly, and lack timely and continuous data collection. To address these challenges and fully leverage remote sensing big data and cloud computing platforms like Google Earth Engine (GEE), this paper developed an algorithm for Auto-Generating Winter Wheat Samples for mapping (AGWWS). The AGWWS utilizes historical samples to determine the optimal migration threshold by measuring Spectral Angle Distance (SAD), Euclidean Distance (ED), and Near-Infrared band Difference Index (NIRDI). This facilitates the auto-generation of winter wheat sample sets for the years 2000, 2005, 2010, 2015, and 2021. Approximately two-thirds of the samples were allocated for training, with the remaining one-third used for validating the mapping method, employing the One-Class Support Vector Machine (OCSVM). The Huang–Huai–Hai (HHH) Plain, a major winter wheat production region, was selected to perform the algorithm and subsequent analysis on. Different combinations of the hyper-parameters, gamma and nu, of the OCSVM based on the Gaussian Radial Basis Function Kernel were tested for each year. Following correlation analysis between the winter wheat area derived from the generated maps and the national statistical dataset at the city level, the map with the highest corresponding R2 was chosen as the AGWWS map for each year (0.77, 0.77, 0.80, 0.86, and 0.87 for 2000, 2005, 2010, 2015, and 2021, respectively). The AGWWS maps ultimately achieved an average Overall Accuracy of 81.65%. The study then explores the Non-Grain Production of Winter Wheat (NGPOWW) by analyzing winter wheat change maps from 2000–2005, 2005–2010, 2005–2010, and 2015–2021 in the HHH Plain. Despite an overall increase in the total planted area of winter wheat, the NGPOWW phenomena has led to concerning winter wheat planting marginalization. Compensatory winter wheat areas are notably situated in mountainous and suburban cultivated lands with low qualities. Consequently, despite the apparent expansion in planted areas, winter wheat production is anticipated to be adversely affected. The findings highlight the necessity for improved cultivated land protection policies monitoring the land quality of the compensation and setting strict quota limits on occupations.