<b><i>Introduction:</i></b> The rising number of complaints against dentists in Saudi Arabia was the main motivator to conduct this study, which aimed to assess the level of knowledge regarding health professional regulations among dentists, identify the associated factors, and explore the consequences of malpractice experience. <b><i>Methods:</i></b> This was a cross-sectional study conducted between February and July 2022 among dentists working at public or private dental clinics in Saudi Arabia and who had medical malpractice insurance coverage. To conduct the research, a predestined questionnaire comprised three sections: section 1 included 13 questions aimed to assess the knowledge related to the health professional regulations in Saudi Arabia; section 2 evaluated the most significant changes in providing dental care as a result of complaint experience; and section 3 assessed the impact of the complaint on dentists’ professional practice and physical and psychological conditions. <b><i>Results:</i></b> The study included 148 dentists who responded to the questionnaire. The dentists’ median score of their knowledge concerning legal health regulations in Saudi Arabia was 7 (range: 6–9) out of 13. The median score was higher among dentists who had been sued compared with those who had never been sued (8 [IQR: 7–9.75] vs. 7 [IQR: 5.25–9], respectively), although no significant difference was detected (p > 0.05). A significantly higher median score (p = 0.029) was recorded among male dentists (median = 7 [IQR: 6–10]) compared to female dentists (median = 7 [IQR: 5–8]). <b><i>Conclusion:</i></b> The overall level of knowledge of dental care legal regulations among the included dentists was good to some extent. Several dentists with a history of malpractice changed their behavior toward patients. This change in behavior was more common among dentists who had been previously sued.