The strength of the thiol-gold interactions provides the basis to fabricate robust self-assembled monolayers for diverse applications. Investigation on the stability of thiol-gold interactions has thus become a hot topic. Here we use atomic force microscopy to quantify the stability of individual thiol-gold contacts formed both by isolated single thiols and in self-assembled monolayers on gold surface. Our results show that the oxidized gold surface can enhance greatly the stability of gold-thiol contacts. In addition, the shift of binding modes from a coordinate bond to a covalent bond with the change in environmental pH and interaction time has been observed experimentally. Furthermore, isolated thiol-gold contact is found to be more stable than that in self-assembled monolayers. Our findings revealed mechanisms to control the strength of thiol-gold contacts and will help guide the design of thiol-gold contacts for a variety of practical applications.