Background: With the increasing recognition that leadership skills can be acquired, there is a heightened focus on incorporating leadership training as a part of graduate medical education. However, there is considerable lack of agreement regarding how to facilitate acquisition of these skills to resident, chief resident, and fellow physicians. Methods: Articles were identified through a search of Ovid MEDLINE, EMBASE, CINAHL, ERIC, PsycNet, Cochrane Systemic Reviews, and Cochrane Central Register of Controlled Trials from 1948 to 2019. Additional sources were identified through contacting authors and scanning references. We included articles that described and evaluated leadership training programs in the United States and Canada. Methodological quality was assessed via the MERSQI (Medical Education Research Study Quality Instrument). Results: Fifteen studies, which collectively included 639 residents, chief residents, and fellows, met the eligibility criteria. The format, content, and duration of these programs varied considerably. The majority focused on conflict management, interpersonal skills, and stress management. Twelve were prospective case series and three were retrospective. Seven used pre-and post-test surveys, while seven used course evaluations. Only three had follow-up evaluations after 6 months to 1 year. MERSQI scores ranged from 6 to 9. Conclusions: Despite interest in incorporating structured leadership training into graduate medical education curricula, there is a lack of methodologically rigorous studies evaluating its effectiveness. High-quality well-designed studies, focusing particularly on the validity of content, internal structure, and relationship to other variables, are required in order to determine if these programs have a lasting effect on the acquisition of leadership skills.