The structures and the wear data of 47 different organic compounds as lubricant base oils were included in a comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA)–quantitative structure tribo-ability relationship (QSTR) model. CoMFA- and CoMSIA-QSTR models illustrate good accuracy, robustness, and predictability, with the latter more accurate than the former. CoMFA-QSTR with both steric and electrostatic fields: R2 = 0. 958, R2(LOO) = 0.958, and q2 = 0.625; with only a steric field: R2 = 0.987, R2(LOO) = 0.987, and q2 = 0.692. CoMSIA-QSTR with a steric field: R2 = 0.924, R2(LOO) = 0.923, and q2 = 0.898, whereas CoMSIA-QSTR with a hydrophobic field gave R2 = 0.985, R2(LOO) = 0.985, and q2 = 0.899. QSTR with CoMFA and CoMSIA shows a strong correlation to wear scar diameter scales (WDS), and builds statistical and graphical models that relate the wear properties of molecules to their structures.