Laura A. Huppert, MD; Lekshmi Santhosh, MD, MAEd; Jennifer M. Babik, MD, PhD March 19, 2021, was Match Day. This year, a record-setting 33 353 participants were successfully matched to first-year residency positions. Overall, 92.8% of graduating US MD students were matched to a residency training program—a rate similar to the historical average of 93% to 94%—while 89.1% of graduating osteopathic medical students were matched, a slight decline from 90.7% the previous year. 1 Although the outcome of this residency application season was similar to those before, the processes leading to it were unlike any other year. The COVID-19 pandemic disrupted all aspects of the 2020-2021 residency application cycle. This year, essentially all residency interviews were conducted virtually; away rotations were suspended; both standardized test score reporting and the season start date were delayed; and applicants and programs alike encountered significant uncertainty about how best to optimize their outcomes. Reflecting on the 2020-2021 residency application cycle shows both lessons learned and lingering problems that must be addressed.