Evidence-informed data may help students matching into competitive residency programs guide curricular activities, extracurricular activities, and residency career choices. We aimed to examine the characteristics of students applying to competitive surgical residencies and identify predictors of matching success. We identified the five lowest match rates for the surgical subspecialities listed in the 2020 National Resident Matching Program report to define a surgical residency as competitive. We analyzed a database from 115 United States medical schools regarding application data from 2017 to 2020. Multilevel logistic regression was used to determine predictors of matching. Statistical significance was set at  < 0.05.A total of 1,448 medical students submitted 25,549 applications. The five most competitive specialties included were plastic surgery ( = 172), otolaryngology ( = 342), neurological surgery ( = 163), vascular surgery ( = 52), orthopedic surgery ( = 679), and thoracic surgery ( = 40). We found that medical students with a geographical connection (adjusted OR, 1.65 [95% CI, 1.41 to 1.93]), and students who did an away rotation at the applied program (adjusted OR, 3.22 [95% CI, 2.75 to 3.78]) had statistically significantly increased odds of matching into a competitive surgical specialty. Furthermore, we found that students with a United States Medical Licensing Examination (USMLE) Step 1 score below 230 and Step 2 Clinical Knowledge (CK) score below 240 had increased odds of matching if they completed an away rotation at the applied program. Completing an away rotation and geographical connection to the institution may contribute more than academic criteria for selection into a competitive surgical residency after an interview. This finding may be due to less variation in academic criteria among this pool of high-performing medical students. Students with limited resources who apply to a competitive surgical specialty may be at a disadvantage given the financial burden of an away rotation.