The expansion of irrigated agriculture during the Soviet Union (SU) era made Central Asia a leading cotton production region in the world. However, the successor states of the SU in Central Asia face on-going environmental damages and soil degradation that are endangering the sustainability of agricultural production. With Landsat MSS and TM data from 1972/73, 1977, 1987, 1998, and 2000 the expansion and densification of the irrigated cropland could be reconstructed in the Kashkadarya Province of Uzbekistan, Central Asia. Classification trees were generated by interpreting multitemporal normalized difference vegetation index data and crop phenological knowledge. Assessments based on image-derived validation samples showed good accuracy. Official statistics were found to be of limited use for analyzing the plausibility of the results, because they hardly represent the area that is cropped in the very dry study region. The cropping area increased from 134,800 ha in 1972/73 to 470,000 ha in 2009. Overlaying a historical soil map illustrated that initially sierozems were preferred for irrigated agriculture, but later the less favorable solonchaks and solonetzs were also explored, illustrating the strategy of agricultural expansion in the Aral Sea Basin. Winter wheat cultivation doubled between 1987 and 1998 to approximately 211,000 ha demonstrating its growing relevance for modern Uzbekistan. The spatial-temporal approach used enhances the understanding of natural conditions before irrigation is employed and supports decision-making for investments in irrigation infrastructure and land cultivation throughout the Landsat era.