This study aimed to investigate the possible factors affecting dentists’ behavior relating to performing oral cancer examinations as part of routine clinical examination. A total of 95 direct clinical observation sessions—utilizing an instrument consisting of 19 evidence-based observational criteria for oral cancer examinations—were observed by four calibrated dentists. Thirty-two final-year students, 32 interns, and 31 faculty members of Jazan Dental School were examined between April 9 and May 4, 2017. A descriptive analysis was conducted to investigate the frequencies/percentages of the performed observing criteria by all examiners. ANOVA and Tukey tests were carried out to investigate the difference between the examiner groups. A total number of 32 patients participated in the study, whereby each patient was examined by three different examiners from each group, as well as by the attending observer/s. Fewer than 50% of the examiners performed the clinical steps necessary for an oral cancer examination—for example, taking into account past medical history, as well as extra and intra-oral examinations. More than 90% of the examiners examined hard tissue, whereas fewer than 30% of them educated their patients about possible risk factors. A significant difference between examiner groups was found in favor of faculty members. A gap between knowledge and actual practice of oral cancer examinations was evident: majority of participants failed to perform the necessary steps for an oral cancer examination. Previous experience and confidence in performing oral cancer examination are possible explanations for the dentist’s behavior toward oral cancer examination.