Fretting fatigue is a well-known and dangerous damage mode that occurs on the mating surfaces of mechanical components, mainly promoted by a combination of stress distribution, contact pressure distribution, and relative sliding (micro)motion between the surfaces. However, predicting this mechanism is challenging, necessitating specific studies for each assembly due to variable influences. This article presents a methodology for evaluating fretting fatigue damage at the contact between a titanium connecting rod big end and the bearing, adopting the Ruiz parameter as a quantifying damage index. For this purpose, a thermal-structural finite element model is prepared. In particular, the machining and assembly of the split conrod big end are simulated, considering thermal effects. A full engine cycle is first simulated, and results are used for identifying critical instants to be considered for accurate yet computationally efficient calculations. The dependence of fretting fatigue on three factors is studied: bearing crush, bolts tightening torque, and friction coefficient between the big end and the bearing. In summary, the damage increases with a higher crush and friction, while tightening torque has marginal effects. Following a 20% increase in crush height, a corresponding 10% rise in the Ruiz parameter is observed. Conversely, reducing the crush height by 20% leads to an approximately 8% decrease in the Ruiz parameter. When the influence of the bolt preload is taken into account, only a marginal 1% increase of the Ruiz parameter is recorded despite a 30% rise in preload. Evaluating the impact of the friction coefficient on the Ruiz parameter reveals an almost linear relationship. These findings suggest that adjusting the screw preload can enhance the hydrodynamic behavior of the bearing without exacerbating fretting. Furthermore, exploiting the linear correlation between Ruiz and the friction coefficient allows for the generalization of results obtained with specific coefficient values. This methodology can, therefore, serve as a valuable reference for adjusting different variables during the initial design phases of a four-stroke internal combustion engine’s dismountable connecting rod.