There is a connection between the efficiency of oils and their wear and/or surface damage protective properties, an area not so well described in the literature. One such damage mode is macroscale contact fatigue on gear tooth flank surfaces, also called pitting. The present study is aimed at investigating the correlation between gear oils' physical properties, important in terms of gear transmission losses, and pitting life. Eight gear oils were formulated giving different combinations of base oil, viscosity, and concentration of friction modifiers. All eight oils also contained an additive package designed to meet GL-5 specifications. This study consists of three parts. In the first, the oils' physical properties were measured using a set of bench tests. In the second, the pitting lives of the oils were evaluated using rolling four-ball tests. The third part deals with the correlation between the measured physical properties of the oils and their pitting lives. This is achieved through multiple linear regression, with a view to finding the salient properties that have a significant influence on pitting life. The results show that gear oils' physical properties do have a large influence on the pitting lives. Oil properties that lower interfacial tangential stresses are beneficial in enhancing pitting life.