The parallel steel wires used in arch bridge suspenders experience random corrosion damage on their surfaces during service. Corrosion damage, including micro-cracks, pitting, and a combination of both, leads to significant stress concentration under axial loading, which affects the performance of the steel wires. The change in the stress field caused by surface damage alters the stress intensity factor at the crack tip, and the presence of adjacent crack tips significantly amplifies the stress intensity factor, thereby accelerating crack propagation. The development of small surface damages in the steel wires is difficult to control and observe through experiments. By utilizing finite element methods for simulation, it is possible to intuitively analyze the crack propagation process, the trend of stress changes at the crack tip, and the interaction between damages. Numerical simulation results based on Paris’ law indicate that corrosion pits have a certain impact on the stress intensity factor at the crack tip. The propagation process of coplanar double cracks is highly sensitive to the initial crack size and the distance between adjacent crack tips. When the crack spacing is less than the crack depth, the stress intensity factor at the adjacent crack tips exhibits significant amplification. Based on this phenomenon, the coplanar double-crack system can be simplified to a complete single crack for analysis. By comparing the fatigue life of the double-crack system with that of the equivalent single crack, the effectiveness of the simplification rule has been validated.