Objective Structured Clinical Examinations (OSCEs) are routinely used in healthcare education programs. Traditionally, students undertake OSCEs as face-to-face interactions to assess competency in soft skills. Due to physical distancing restrictions during COVID-19, alternative methods were required. This study utilized a mixed-method design (online survey and interviews) to evaluate second-year pharmacy students’ and examiners’ experiences of their first virtual OSCEs in Australia. A total of 196 students completed their first virtual OSCE in June 2020 of which 190 students completed the online survey. However, out of the 190 students, only 88% (n = 167) consented to the use of the data from their online survey. A further 10 students and 12 examiners were interviewed. Fifty-five students (33%) who participated in the online survey strongly agreed or agreed that they preferred the virtual experience to face-to-face OSCEs while 44% (n = 73) neither agreed nor disagreed. Only 20% (n = 33) felt more anxious with the virtual OSCEs. Additionally, thematic analysis found non-verbal communication as a barrier during the OSCE. Positive aspects about virtual OSCEs included flexibility, decreased levels of anxiety and relevance with emerging telehealth practice. The need for remote online delivery of assessments saw innovative ways of undertaking OSCEs and an opportunity to mimic telehealth. While students and examiners embraced the virtual OSCE process, face-to-face OSCEs were still considered important and irreplaceable. Future opportunities for OSCEs to be delivered both face-to-face and virtually should be considered.