There is provided a leakage oil detection system including: a measurement device that includes a light source that causes a measured object which includes a leakage oil attachment part to be irradiated with ultraviolet rays, and an imaging device that detects fluorescence emitted from the leakage oil attachment part which is irradiated with the ultraviolet rays, and performs imaging on the measured object; and an analysis device that includes a driving control unit that controls operations of the light source and the imaging device, a recording unit that records an imaged image of the measured object which is imaged by the imaging device, and an image processing unit that calls the imaged image which is recorded in the recording unit and performs an image process. The imaging device controls exposure according to an exposure control value provided in the imaging device, and the analysis device calls the imaged image which is recorded in the recording unit for the image processing unit, calculates brightness values of respective pixels in the imaged image, determines a maximum brightness value which has the largest value among the brightness values of the respective pixels, compares the maximum brightness value with a reference brightness value which is determined in advance, acquires the exposure control value of the imaging device, in which the nearest brightness value that is smaller than the reference brightness value is acquired, images the measured object again by the imaging device using the acquired exposure control value, transmits the acquired image to the image processing unit, and detects leakage oil by performing the image process by the image processing unit.