Future weather and climates, especially rainfall, are expected to have larger variability in the Southern Plains of the United States. However, the degree and timing of environmental variability that affect productivity of pastures managed differently have not been well studied. We examined the impacts of environmental variability on grassland productivity using 17 years of gross primary productivity (GPP) data for co-located native and managed prairie pastures in Oklahoma. We also considered the interactive effects of management factors and environmental variability into the regression models and identified the critical temporal windows of environmental variables (CWE) that influence annual variability in GPP. Managed pasture (MP) showed greater variability of GPP than did native pasture (NP), particularly with reduced GPP in drought years. The resilience of native prairies under unfavorable climate extremes was evident by lower GPP anomalies in NP than MP during the 2011–2012 drought. Although both pastures experienced the same degree of environmental variability, the CWE affecting GPP was significantly different between NP and MP due to the modulating impact of management practices on the responses of GPP. Not only the range but also the timings of the CWE were different between NP and MP as MP was more responsive to the spring temperature and fall rainfall. Our findings warrant the incorporation of MP as a different commodity from NP when accounting for the ecosystem responses to environmental variability in global climate models.