We analyzed application and match rates for pain medicine training in the United States and hypothesized that there would be (1) greater growth in the number of training positions than applicants, (2) higher match rates among US allopathic graduates relative to non-US allopathic graduates, and (3) greater number of unfilled training positions over time. Retrospective, cross-sectional study of all applicants for pain medicine training in the United States. National Resident Matching Program data were obtained over a ten-year period (2014-2023). Match rates and applicant-to-position ratios were calculated and compared over time with linear regression. Comparisons were made with chi-square tests. Growth in the number of annual training positions (261-377, 44% increase) exceeded growth in the number of interested applicants (398-415, 4% increase) (P < .001). Annual applicant-to-training position ratios decreased (1.5-1.1, P < .001). The representation of US allopathic graduates among incoming pain medicine fellows decreased over the study period (73%-58%, P < .001) while US osteopathic graduates increased (9%-28%, P < .001).Match rates increased for both US allopathic graduates (71%-91%, P < .001) and non-US allopathic graduates (51%-81%, P < .001). From 2018 to 2023, US allopathic graduates (79%) had higher match rates than US osteopathic graduates (60%, P < .001) and international medical graduates (57%, P < .001). More available annual training positions went unfilled over the study period (2%-5%, P = .006). Stagnant annual applicant volume and increasing number of available training positions have led to increasing match rates for pain medicine fellowship training. Fewer US allopathic graduates are pursuing pain medicine training. The increasing percentage of unfilled training positions warrants ongoing surveillance.