Volatile organic contamination is known to be one of the factors to cause the failure of head-disk interface (HDI). Therefore, reduction of its harmful effects and improvement of the stability and reliability of HDI is becoming an important issue. In this study, the effects of some model compounds of volatile organic contamination on the tribological characteristics of HDI were systematically investigated using a contact start/stop (CSS) tester. The slider surface after the CSS tests was analyzed using Time-of-Flight Secondary Ion Mass Spectroscopy (TOF-SIMS). Transfer of lubricating oil onto the slider surface was detected after the CSS tests. The organic contaminants promoted the transfer and resulted in high and unstable friction force. Fluorinated self-assembled monolayers (SAMs) were applied on the slider surface for reducing the transferred amount of the lubricating oil. Tribological performance of the slider coated with the SAMs and the transfer amount of lubricating oil onto the slider surface in the presence of contaminant was investigated. The friction force was low and stable in the case of the SAMs coated slider even under environmental contaminant. This result could be explained by the reduction of the transferred lubricating oil because the SAMs that coated on the slider surface were low surface energy.