To find materials that meet the future requirements of increasing load density in wind turbine gear structures, the commonly used reference material, 18CrNiMo7-6, and another high-strength steel were analysed. Their fatigue properties were studied through rolling contact fatigue (RCF) and gear tooth root bending fatigue (TRBF) tests. The reference steel exhibited better fatigue performance under RCF conditions compared to the new steel; however, it was outperformed by the new steel under TRBF conditions. This study aims to understand gear contact fatigue at the microscopic level, moving beyond the macroscopic focus that dominates current research literature. To establish the causal link between the varied fatigue performance observed in these materials, we proposed a multiscale modelling workflow based on crystal plasticity. This crystal plasticity framework is combined with the fatigue indicator parameter (FIP) to explore the fatigue resistance of materials subjected to RCF and TRBF conditions. Emphasis has been placed on the role of retained austenite (RA) in fatigue performance. Utilizing representative elementary volumes (REVs) generated based on statistically representative crystallographic features and measured size distribution of RA, we examined the effects of various RA levels on fatigue resistance. Our findings reveals that the fatigue damage accumulation is significantly influenced by the level of RA. Different fatigue damage accumulation behaviours were observed under RCF and TRBF conditions. These insights offer new perspectives on RA’s role in fatigue resistance and highlight its complex influence under varied loading conditions.