Introduction: As healthcare becomes increasingly digital, undergraduate medical students receive limited formal training in digital healthcare technologies (DHTs). Additionally, stakeholders' perspectives on essential digital health competencies (DHCs) across generations remain underexplored. This comparative study aims to identify knowledge gaps, inform evolving expectations, and promote continuous learning by comparing medical students' and senior clinicians' views on essential DHCs in Singapore. Methods: Individual semi-structured interviews were conducted with medical students, clinical educators, and clinical teachers. Clinical-year medical students from all three local medical schools were recruited using convenience and snowball sampling, while purposive sampling ensured diverse representation of clinicians across Singapore's public healthcare organisations, focusing on those engaged in education-related activities. Data were collected from September 2020 to February 2023 until thematic saturation was achieved, and analysed using qualitative thematic analysis. Results: Sixty-three participants took part, including 30 medical students, 12 clinical educators and 21 clinical teachers. All clinicians had more than 10 years of clinical experience and came from 24 different disciplines and 12 healthcare institutions. The findings showed unanimous support for integrating electronic health records in patient communication, and training in DHTs like telemedicine and point-of-care ultrasound. Discrepancies emerged; clinicians prioritised physical examination, while students viewed it as potentially replaceable by DHTs. Furthermore, while students valued healthcare-related smartphone applications in patient care, few clinicians shared this view, citing privacy and security concerns. Conclusion: Evaluating stakeholders' perspectives highlights evolving clinical skills and essential DHCs for medical students, potentially informing global DHC training programmes.