Background: The purpose of this paper is to do a cross-sectional analysis to evaluate the impact of the Coronavirus Disease 2019 pandemic on Dental Match Residency statistics from the year 2019-2023. Methods: The Dental Match Residency statistics available from the Dental Match website were analyzed from years 2019-2023 to evaluate the impact of pre-pandemic (2019-2020), pandemic (2021, 2022) and post-pandemic year trends (2023). Important trends were evaluated and summarized using graphs, descriptive statistics, and two sample tests for proportions (chi-square test) comparing different pairs of years. Results: Total Match participants increased in 2021 followed by a drop in 2022, and 2023 despite an increase in total MATCH positions offered in 2023. The percentage of unmatched applicants to total applicants and the ratio of total applicants to total positions peaked in 2021 compared to other study periods (all yearly comparisons p < 0.001). The ratio of graduates who were not fresh out of dental school to total graduates has seen a small steady increase since 2021 (p > 0.06). Participants ranking more than one type of residency program saw an increase in 2021 which decreased in 2023 (p < 0.05). Conclusions: The Dental Match statistics have undergone several distinct changes and trends during the pre-pandemic, pandemic, and post-pandemic years. Further specific residency-based MATCH data from the USA and equivalent sources around the world needs to be investigated to understand the underlying trends and to guide future policymaking for post-graduate dental specialty training especially as it relates to specific factors such as job market, perceived quality of education, economic and geopolitical factors.