In this study, premature damage in cylindrical roller bearings made of 100Cr6 (SAE 52100) was investigated. For this purpose, full bearing tests were carried out using two different lubricant formulations with similar viscosities. Published research has pointed out the occurrence of tribo-chemical reactions that cause lubricant degradation and the release of hydrogen in tribo-contact. Hydrogen content measurements were conducted on tested samples, and these measurements showed dependence on the lubricant formulations. Hydrogen diffusion and trapping were identified as significant factors influencing premature damage. The measurement of trapping energies was conducted by thermal desorption spectroscopy, whereas residual stresses, which influence hydrogen diffusion and accumulation, were measured using X-ray diffraction. The measured trapping energies indicated that rolling contact caused the creation and release of hydrogen traps. Over-rolling resulted in changes in residual stress profiles in the materials, demonstrated by changes in stress gradients. These can be directly linked to subsurface hydrogen accumulation. Hence, it was possible to determine that the location of the microstructural damage (WEC) was correlated with the residual stress profiles and the subsurface von Mises stress peaks.