Background: Medico-legal complaints against physicians are a significant source of anxiety and could be associated with defensive medical practices that may correlate with poor patient outcomes. Little is known about patient concerns brought to regulatory bodies and courts against dermatologists in Canada. Objective: To characterize factors contributing to medico-legal complaints brought against dermatologists in Canada. Methods: The Canadian Medical Protective Association (CMPA) repository was queried for all closed cases involving dermatologists over the past decade. Aggregate, anonymized data was reviewed and case outcomes, patient harm, and contributing factors were extracted. Results: Nearly one-fifth of all dermatologists who are CMPA members have been named in at least one medico-legal case between 2013 to 2022. A total of 396 civil-legal actions or College complaint cases involving dermatologists were closed at the CMPA during this timeframe. The most common patient allegations were deficient assessment (34%), diagnostic error (28%), and unprofessional manner (22%). Nearly half of patients experienced a harmful event, the majority of which were asymptomatic or mild. The most frequently identified contributing factors related to providers were poor clinical decision making (n = 73), lack of situational awareness (n = 67), and conduct and boundary issues (n = 59). Team factors included a breakdown of communication with patients (n = 124). Conclusions: Improved communication with patients for informed consent, treatment plans, clinical follow-up, and documentation of thorough clinical patient assessments can improve patient satisfaction and health outcomes, and mitigate dermatologists’ medico-legal risk.