Context Medical students and graduates apply for post-graduate year-one positions every year through the Single Accreditation System (SAS) National Residency Match Program (NRMP). New opportunities have arisen for osteopathic graduates through the transition to a single match. There is a paucity of information evaluating the effects of this single match on osteopathic (DO) and allopathic (MD) candidates in relation to match rates in competitive surgical sub-specialties such as neurosurgery, thoracic surgery, vascular surgery, otolaryngology (ENT), plastic surgery, orthopedic surgery, and general surgery. Objectives This paper utilizes published data to accomplish three tasks. Firstly, it investigates the effects of the SAS on DO and MD match rates in surgical subspecialties of neurosurgery, thoracic surgery, vascular surgery, ENT, plastic surgery, orthopedic surgery, and general surgery. Secondly, it investigates whether program director credentials and impressions correlate with the match rates of DO or MD candidates in each of these specialties. Finally, it discusses solutions for addressing ways to improve match outcomes for all candidates. Methods Previously published NRMP, National Matching Services, and Accreditation Council for Graduate Medical Education websites were queried for the number of DO and MD senior applicants for each position, match success rates, program director impressions, and program director credentials for the years 2018-2023. Match success rates were defined as a ratio of the number of candidates that applied to the number who successfully matched. Data were analyzed using descriptive statistics, chi-squared testing, student t-tests, and linear regression where appropriate. A p-value of less than 0.05 was considered significant. Results From 2020-2023, an increasing proportion of DO residents applied for the selected surgical subspecialties, increasing from 599 applicants in 2020 to 743 candidates in 2023. Overall match rates for DOs remain significantly lower than MD match rates for each of these specialties as well as overall (p-values all <0.05) with summative match rates of 52.89% for DOs compared to 73.61% for MDs in 2023 for the selected surgical subspecialties. From 2020 to 2023 match rates were 30.88% for DOs compared to 74.82% for MDs in neurosurgery, 16.67% versus 46.45% (DO vs MD) in thoracic surgery, 4.17% vs 68.84% (DO vs MD) in plastic surgery, 57.62% vs 73.18% (DO vs MD) in general surgery, 23.21% vs 74.18% (DO vs MD) in vascular surgery, 53.10% vs 72.57% (DO vs MD) for ENT, and 56.92% vs 72.51% (DO vs MD) for orthopedics. There was a statistically significant correlation between the proportion of DO program directors with the rate of DOs matching in the associated specialty (p=0.012). Conclusion There were significantly lower rates for DO candidates compared to MD candidates matching into selected surgical subspecialties of neurosurgery, thoracic surgery, vascular surgery, ENT, plastic surgery, orthopedic surgery, and general surgery. This may be addressed through increasing advocacy at local and national levels, improving mentorship, increasing DO medical student exposure to surgical subspecialties, and ensuring increasing selected surgical subspecialty involvement in teaching these diverse DO applicants in order to strengthen medicine and continue to address predicted growing physician shortages.