Background: The secondary-to-tertiary education transition is a significant milestone in the students’ academic journeys. This is particularly relevant to entry into medical schools, which is characterized by multiple stressors. Although this crucial transition has been repetitively explored, the concept of proactively intervening to support this transition, by fostering Self- Regulated Learning, is still novel. Accordingly, through this study, the authors investigate the efficacy of an online Multi-dimensional Resilience Building Intervention and analyse the association between the students' proficiency of selected skill sets and their academic performance over time. Methods: A retrospective longitudinal study was conducted on one cohort of undergraduate medical students. The students were offered an online learning and development intervention around four skill sets during the first curricular year of an undergraduate Bachelor of Medicine, Bachelor of Surgery program. Deidentified data, related to the students' proficiency of the four selected skill sets and the students’ academic performance: Grade-Point-Average, were retrieved. The data was analysed using SPSS for Windows version 27.0. Results: Out of the 63 admitted students, 28 participated in the offered intervention. The correlational analysis showed how increase in the overall score of skill sets proficiency was significantly associated with Year 1 GPA and cGPA. The students’ proficiency in the respective skill sets, however, was independent from their Year 2 GPA. Additionally, the performance of the students seemed to be not associated with their proficiency scores in each of the selected skill sets, independently. Conclusions: The innovative intervention of developing selected skill sets constituted an efficacious bridge to facilitate the secondary-to-tertiary education transition. Adapting such a multi-dimensional, resilience building intervention holds the potential of facilitating the students’ entry into medical school and improving their performance. As the medical student progresses, the acquired skills need to be continuously reinforced and effectively built upon.