An innovative computing tool (RFPA2D-Cycle) was developed for modelling progressive damage and failure of rock under continuous cyclic loading. Firstly, an assumption of linear strength degradation of the mesoscopic elements was proposed by taking stress level and upper and lower limit stresses into consideration. Secondly, the assumption was then implemented into the Rock Failure Process Analysis (RFPA2D) to form the developed computing tool—RFPA2D-Cycle code, which is capable of simulating progressive damage of rock under cyclic loading. Thereafter, to examine reliability of the newly developed RFPA2D-Cycle, cyclic loading tests for sandstone samples were numerically reproduced by establishing a two-dimensional axisymmetric model. Finally, the RFPA2D-Cycle code was further utilized to numerically investigate damage progressivity of underground tunnels induced by remote vertical cyclic loading. The results demonstrated that the newly developed RFPA2D-Cycle code, albeit with limitations, may have potential application in understanding of damage and failure mechanisms of rock subjected to cyclic loading. This innovative computing tool may also be valid to predict the impact of cyclic loading on mechanical behaviors and responses, and be appropriate for analyzing stability in the design and construction of rock engineering projects.