Oil-soluble ionic liquids (ILs) have recently been demonstrated as effective lubricant additives of friction reduction and wear protection for sliding contacts. However, their functionality in mitigating rolling contact fatigue (RCF) is little known. Because of the distinct surface damage modes, different types of surface protective additives often are used in lubricants for sliding and rolling contacts. Therefore, the lubricating characteristics and mechanisms of ILs learned in sliding contacts from the earlier work may not be translatable to rolling contacts. This study explores the feasibility of using phosphonium-phosphate, ammonium-phosphate, and phosphonium-carboxylate ILs as candidate additives in rolling-sliding boundary lubrication, and results suggested that an IL could be either beneficial or detrimental on RCF depending on its chemistry. Particularly, the best-performing phosphonium-phosphate IL at 2% addition made a low-viscosity base oil significantly outperform a more viscous commercial gear oil in reducing the RCF surface damage and associated vibration noise. This IL generated a thicker, smoother, and more homogeneous tribofilm compared with commercial additives, which is likely responsible for the superior RCF protection. Results here suggest good potential for using appropriate IL additives to allow the use of low-viscosity gear and axle fluids for improved efficiency and durability.