Wire ropes in marine applications often encounter relatively fast and noticeable wear, a result of the fatigue to which they are exposed coupled with harsh operational conditions. This paper addresses some of the aspects of fatigue damage that occur in wire ropes. Using the finite element method, stress and fatigue analysis of three different design types (6 × 7, 7 × 7, 8 × 7) of wire rope is performed. The size of the wire rope cross-section area is varied in order to simulate the progressive damage of the wires so that consequential stress levels and remaining fatigue life can be numerically predicted. The aim was to provide a better understanding of the mechanical behavior of damaged wire ropes under various conditions, since an appropriate choice of wire rope design could then be made from engineering and economic points of view. Additionally, potential failures can be predicted, resulting in effective maintenance and the avoidance of potential risks of rope failure, especially important regarding economical and safety aspects of transportation in the marine industry.