The Canadian residency match process has been dramatically restructured due to COVID-19. The impact of these changes on specialty choice and access to career-development opportunities among Canadian medical students remains largely unknown. The objective of this study was to assess whether students’ strategy and level of confidence entering the Canadian residency match have changed as a result of the pandemic. A 28-item online survey was distributed to Canadian medical students from the classes of 2021-2024, as well as the class of 2020 graduates planning to enter the 2021 CaRMS (Canadian Resident Matching Service) match. The survey was developed based on existing literature and included questions on demographics, access to educational opportunities, and personal strategies for matching. Descriptive statistics, t-tests, and Spearman’s correlations were used to analyze the data. Eleven percent of respondents reported a change in specialty preference due to COVID-19. Forty-three percent of respondents reported changing their strategy for the CaRMS match. Respondents interested in a surgical specialty were more likely to report a change in their match strategy (p = .0150), including applying to more programs (p = .0012) and exploring other specialties (p = .0118). Clerks were also more likely to report a change in their matching strategy (p = .0195) and specialty choice (p = .0194) compared to pre-clerks. Medical students felt that COVID-19 negatively impacted their ability to access scholarly opportunities and confidence regarding the match, which may have long-term implications for trainee well-being, residency match logistics, and long-term physician resource planning.