After pre-fatigue cycles at different strain amplitudes with different N/Nf values (33.3%, 50%, and 75%), specimens of HRB335 steel were subjected to uniaxial tension until failure. By this method the mechanical properties of the specimens after pre-fatigue testing were measured, and the fracture morphology and microscopic morphology in the vicinity of the specimen’s neck surface near the fracture were observed. The verification of the characteristics to be used to estimate the damage caused during the loading cycles was conducted. By observing optical microscope images of the surface area near the neck of the specimens, it was found that the images of surface cracks were significantly different and strongly depended on the number of pre-fatigue cycles the specimen had undergone. In response to this phenomenon, both the microscopic images taken directly from the photos of the surface crack distribution and the binary images based on them were statistically analyzed, and then a parameter, S, denoted as the “unit crack area”, characterizing the cumulative fatigue damage was suggested. Furthermore, the test procedure and the calculation formula for determining the image parameters were summarized, and a method for evaluating the remaining life of steel after low-cycles of reversed tension and compression was proposed.