The COVID-19 (C19) pandemic introduced challenges in all areas of the Canadian healthcare system. Along with adaptations to clinical care environments, there was increasing concern about physician burnout during this time. The Canadian Association of Medical Oncologists (CAMO) has examined the effects of the pandemic on the medical oncology (MO) workforce. A series of four multiple choice web-based surveys distributed to MOs who were identified using the Royal College of Physicians and Surgeons directory and CAMO membership in May 2020 (S1), July 2020 (S2), December 2020 (S3), and March 2022 (S4). Descriptive analyses were performed for each survey, and a Chi-square test (α = 0.05) was used to assess factors associated with planned change in practice in S4. The majority of respondents work in a comprehensive cancer center S1/S2/S3/S4 (87%/86%81%/88%) and have been in practice >10 years (56%/61%/50%/64%). The most commonly reported personal challenges were physical (60%) and mental (60%) wellness. In S4, 47% of MOs reported dissatisfaction with their current work–life balance. In total, 83% reported that their workload has increased since the beginning of C19, and 51% of MOs reported their future career plans have been impacted by C19. In total, 56% of respondents are considering retiring or reducing total working hours in the next 5 years. Since the onset of the C19 pandemic, there are concerns identified with wellness, increasing workload, and job dissatisfaction among MOs, associated with experienced staff who have >10 years in practice. As rates of cancer prevalence rise and treatments become more complex, it is crucial to address the concerns raised in these surveys to ensure that we have a stable MO workforce in the future.