Introduction: The purpose of this study was to evaluate the use of web-based patient simulations, a whole-task simulation, in oral surgery education for second-year pre-clinical dental students on learning outcomes regarding cognitive, psychomotor and professional interpersonal skills for two topics: local anaesthesia and non-surgical extractions. Materials and Methods: In 2018–19, using an experimental design in a live course, we evaluated two web-based patient simulations on student learning outcomes in an introductory course on oral maxillofacial surgery. The study was repeated across two semesters, Fall (N = 109) and Spring (N = 112), on two different topics, namely local anaesthesia and extractions, respectively. Learning outcomes were evaluated for each topic with two different assessment formats: a student-recorded role-play video project and a fifty-item multiple-choice test. Results: For both topics, local anaesthesia and non-surgical extractions, students in the group, Web Sim, who used the web-based patient simulation over and above the online lesson material earned significantly higher scores in the role-play patient video project compared with the group, No Web Sim, who only used the online lesson materials. However, scores on the fifty-item multiple-choice test did not differ significantly between groups. Conclusions: The results suggest that the web-based patient simulation as a formative assessment type is a useful scaffolding tool for the summative student-recorded role-play patient video project due to the similarity in activity types that support clinical learning objectives.