This paper presents a comparative spatial analysis of urban growth and decline trends in the Indian cities of Cuttack and Bhubaneswar. While geographically proximate, the two cities have experienced markedly different urbanization trajectories shaped by their contrasting origins, planning regimes, and governance. Historic Cuttack reflects an organic morphology with a dense, convoluted core and incremental peripheral growth. Planned Bhubaneswar exhibits an orderly layout with designated functional zones radiating from the center. However, both cities grapple with emerging challenges including deteriorating heritage cores, unmanaged peri-urban expansion, inadequate infrastructure in informal settlements, and spatial disparities. Through mapping of past and projected future patterns, the study delineates locations of growth and decline and their spatial correlations. Findings highlight the significance of economic drivers, land use policies, transportation networks, and other determinants in divergent urbanization. The research recommends integrated planning approaches embracing inclusion, sustainability, and participatory governance principles to address these complex dynamics. By comparing Cuttack and Bhubaneswar, insights emerge to inform policies fostering economically vibrant yet livable cities, applicable across urbanizing India.