Agricultural intensification has resulted in the depletion of groundwater resources in many regions of the world. A prime example is Saudi Arabia, which witnessed dramatic agricultural expansion since the 1970s. To explore the influence of policy interventions aimed to better manage water resources, accurate information on the changes in the number and acreage of center-pivot fields is required. To quantify these metrics, we apply a hybrid machine learning framework, consisting of Density-Based Spatial Clustering of Applications with Noise, Convolutional Neural Networks, and Spectral Clustering, to the annual maximum Normalized Differential Vegetation Index maps obtained from Landsat imagery collected between 1990 to 2021. When evaluated against more than 28,000 manually delineated fields, the approach demonstrated producer’s accuracies ranging from 83.7% to 94.8% and user’s accuracies ranging from 90.2% to 97.9%. The coefficient of determination (R2) between framework-delineated and manually delineated fields was higher than 0.97. Nationally, we found that most fields pre-dated 1990 (covering 8841 km2 in that year) and were primarily located within the central regions covering Hail, Qassim, Riyadh, and Wadi ad-Dawasir. A small decreasing trend in field acreage was observed for the period 1990–2010. However, by 2015, the acreage had increased to approximately 33,000 fields covering 9310 km2. While a maximum extent was achieved in 2016, recent decreases have seen levels return to pre-1990 levels. The gradual decrease between 1990 to 2010 was related to policy initiatives designed to phase-out wheat, while increases between 2010 to 2015 were linked to fodder crop expansion. There is evidence of an agricultural uptick starting in 2021, which is likely in response to global influences such as the COVID-19 pandemic or the conflict in Ukraine. Overall, this work offers the first detailed assessment of long-term agricultural development in Saudi Arabia, and provides important insights related to production metrics such as crop types, crop water consumption, and crop phenology and the overarching impacts of agricultural policy interventions.