Next-generation display technologies, including rollable and foldable displays, are advancing rapidly, enabling innovative and versatile form factors. Flexible displays predominantly utilize materials such as Polyimide (PI), Colorless Polyimide (CPI), and Thermoplastic PolyUrethane (TPU) due to their exceptional flexibility and durability. However, a significant challenge lies in the lack of standardized criteria for evaluating the durability of these flexible substrates. In this study, the durability of these materials under rolling conditions was investigated. This study establishes a standardized methodology for evaluating flexible materials used in rollable displays. Experiments were performed on PI, including rolling and scratch tests with varying indenter sizes. Friction data from the scratch tests, combined with cross-sectional analyses, were examined using optical microscopy and Scanning Electron Microscopy (SEM). The scratch test results revealed that PI films with lower elastic recovery exhibited distinct damage patterns during rolling cycles, especially when smaller indenter radius were used. As the number of rolling cycles increased, the critical force decreased rapidly. This behavior was attributed to the weakening or breaking of atomic bonds within the film. This was further confirmed by SEM images, which revealed delamination of the film from the surface after rolling.