The main goal of this research was to detect oil spills, to determine the oil spill frequencies and to approximate oil leak sources around the Oil Rocks Settlement, the Chilov and Pirallahi Islands in the Caspian Sea using 136 multi-temporal ENVISAT Advanced Synthetic Aperture Radar Wide Swath Medium Resolution images acquired during 2006–2010. The following oil spill frequencies were observed around the Oil Rocks Settlement, the Chilov and Pirallahi Islands: 2–10 (3471.04 sq km), 11–20 (971.66 sq km), 21–50 (692.44 sq km), 51–128 (191.38 sq km). The most critical oil leak sources with the frequency range of 41–128 were observed at the Oil Rocks Settlement. The exponential regression analysis between wind speeds and oil slick areas detected from 136 multi-temporal ENVISAT images revealed the regression coefficient equal to 63%. The regression model showed that larger oil spill areas were observed with decreasing wind speeds. The spatiotemporal patterns of currents in the Caspian Sea explained the multi-directional spatial distribution of oil spills around Oil Rocks Settlement, the Chilov and Pirallahi Islands. The linear regression analysis between detected oil spill frequencies and predicted oil contamination probability by the stochastic model showed the positive trend with the regression coefficient of 30%.