Climate, human disturbances, and management practices jointly control the spatial and temporal patterns of land surface phenology. However, most studies solely focus on analyzing the climatic controls on the inter-annual variability and trends in vegetation phenology. Investigating the main and interacting effects of management practices and climate might be crucial in determining vegetation phenology and productivity. This study examined the impacts of climate and management practices on vegetation phenology and productivity in adjacent native and introduced prairie pastures, which have detailed long-term management records, by combining climate, management, and satellite remote sensing data (e.g., Moderate Resolution Imaging Spectroradiometer (MODIS) and Landsat). Modeled gross primary production (GPP) using vegetation photosynthesis model (VPM) was also included to investigate the dynamics of productivity. When comparing the impacts of the same management practices on different pastures, we used paired comparison, namely, comparing the native and introduced prairies side by side in the same year. The interactions of management practices and climate were investigated through comparing years with similar management but different climate (e.g., years with rainfall or not following baling events) in the same pasture. Results showed that air temperature (Ta) was an important factor in determining the start of the season (SOS) and the length of the season (LOS). Total rainfall (RF) during the annual growing season (AGS, derived from vegetation indices (VIs)) had the largest explanatory power (R2 = 0.53) in explaining the variations in the seasonal sums of VIs. The variations in GPP were better explained by RF (R2 = 0.43) than Ta (R2 = 0.14). Using the thermal growing season (March–October) or AGS climate factors did not show large differences in determining the relationships between phenology, GPP, and climate factors. Drought shortened the LOS and decreased GPP. In terms of management practices, grazing generally reduced the VIs and burning induced early greening-up and enhanced vegetation growth. Drought plus other management practices (e.g., grazing or baling) greatly affected vegetation phenology and suppressed GPP. The negative impacts (i.e., removal of biomass) of grazing on vegetation was compensated by enhanced vegetation growth after good RF. This study demonstrated that the interactions of climate and management practices could be positive (burning plus baling in a good RF year) or negative (grazing/baling plus drought), and can significantly affect vegetation phenology and production.