The Yangtze River Delta Urban Agglomeration (YRDUA), which is located in the convergence zone of “The Belt and Road Initiative”, is one of the regions with the best urbanization foundations in China. Referring to the four five-year plans (China’s national economic plan), this study aimed to investigate the spatiotemporal patterns of urban expansion in the YRDUA from 2000 to 2020. To conduct a long-term analysis of urbanization, an extended time series (2000–2020) of a nighttime light (NTL) dataset was built from the multi-temporal Defense Meteorological Satellite Program’s Operational Linescan System (DMSP-OLS) data (2000–2013), and Suomi National Polar-Orbiting Partnership Visible Infrared Imaging Radiometer Suite (NPP-VIIRS) data (2014–2020); data from these sources are crucial to understanding the urbanization processes in the region in order for more effective decision making to take place. The support vector machine (SVM) method was used to extract urban clusters from the extended time-series NTL data and MODIS NDVI products. The evolution of the urban expansion intensity was detected at city scales, and the inequality of urban growth was demonstrated using the Lorenz curve and Gini coefficient. Finally, a quantitative relationship between urban NTL intensity and socio-economic data was built to explore the main factors that control urban intensity. The results indicated that the urban extents extracted from time-series NTL data were consistent with those extracted from Landsat data, with an average overall accuracy (OA) of 89%. A relatively fast urbanization pace was observed during the 10th five-year plan (from 2000 to 2005), which then declined slightly in the 11th five-year plan (from 2006 to 2010). By the 12th and 13th five-year plan (from 2011 to 2020), urban clusters in all cities tended to grow steadily. Urban expansion has presented a radial pattern around the main cities, with sprawl inequality across cities. The results further revealed that the primary factors controlling NTL brightness were gross domestic product (GDP), total fixed asset investment, tertiary industry, gross industrial output, urban area, and urban permanent residents in city clusters, but the same driving factors had a different contribution order on the NTL intensity across cities. This study provides significant insight for further urbanization study to be conducted in the YRDUA region, which is crucial for sustainable urban development in the region.