The transition to college life is a highly demanding period for all students, especially when enrolling into an academically-challenging field as that of medicine. First-generation medical students represent an overlooked demographic and are thought to be more vulnerable to the stressors of college. This study's aim is to explore the differences between first and continuing-generation medical students in Egypt regarding their academic performance, extracurricular training opportunities and future expectations. Two identical 24-item online questionnaires, in English and Arabic were distributed with five main themes: general demographics, academic performance, extracurricular training opportunities (outpatient clinics, hospitals and operating rooms), future expectations and if participants have relatives in the medical field. Responses from 1652 eligible respondents from all 36 medical universities in Egypt were received. Continuing-generation medical students achieved a higher cumulative grade, with 46.1% getting an "Excellent" grade compared to only 38.4% in the first-generation. The gap between the two groups was best noted in Year 1 (p-value < 0.001), as continuing-generation medical students were almost twice more likely to score an "Excellent" grade [Odds Ratio = 1.85 (1.48-2.31)]. First-generation group had less training opportunities in clinics (p < 0.001) and operating rooms (p < 0.001). There was a significant difference (p < 0.001) across all three clinical settings in regard to how the training opportunity was acquired. The majority of continuing-generation medical students credited their family members for it. Amongst those who wish to travel, the majority of the first-generation medical students plan to pursue their career in the United States; whereas, most of continuing-generation medical students aimed for the Middle East and Western Europe. First-generation medical students had lower grades at first mainly due to their lack of awareness of proper resources that were provided by the families of continuing-generation medical students. However, the challenges posed to first-generation medical students prompted the development of higher resilience, enabling them to catch up and even surpass their continuing-generation counterparts. Continuing-generation medical students obtained further extracurricular training (outpatient clinics and operating rooms), accessed mainly through their family members and connections; whereas, first-generation medical students received most of their training by searching for it themselves.