Image analysis techniques have been applied to measure the displacements, strain field, and crack distribution of structures in the laboratory environment, and present strong potential for use in structural health monitoring applications. Compared with accelerometers, image analysis is good at monitoring area-based responses, such as crack patterns at critical regions of reinforced concrete (RC) structures. While the quantitative relationship between cracks and structural damage depends on many factors, cracks need to be detected and quantified in an automatic manner for further investigation into structural health monitoring. This work proposes a damage-indexing method by integrating an image-based crack measurement method and a crack quantification method. The image-based crack measurement method identifies cracks locations, opening widths, and orientations. Fractal dimension analysis gives the flexural cracks and shear cracks an overall damage index ranging between 0 and 1. According to the orientations of the cracks analyzed by image analysis, the cracks can be classified as either shear or flexural, and the overall damage index can be separated into shear and flexural damage indices. These damage indices not only quantify the damage of an RC structure, but also the contents of shear and flexural failures. While the engineering significance of the damage indices is structure dependent, when the damage indexing method is used for structural health monitoring, the damage indices safety thresholds can further be defined based on the structure type under consideration. Finally, this paper demonstrates this method by using the results of two experiments on RC tubular containment vessel structures.