OBJECTIVE: The purpose of this study was to analyze the trend in subspecialization among men graduating from obstetrics and gynecology residency programs. STUDY DESIGN: Results of the Survey of Residents Completing Training in New York State were analyzed for 1998 to 2003. The proportions of men and women graduating from residency programs and pursuing subspecialty training were compared. Multivariate regression analysis was conducted to analyze trends over time while controlling for confounding variables. RESULTS: Seven hundred thirty-seven Ob/Gyn, 1820 pediatrics, and 5007 internal medicine residents responded. The proportion of male graduating Ob/Gyn residents decreased from 46% to 23% (P < .001). Of those men, the proportion that proceeded with subspecialty training increased from 5.3% to 25.0% (P = .01). Women graduating from an Ob/Gyn residency program displayed a similar but smaller trend towards subspecialization, as did men graduating from pediatrics residencies. Men graduating from internal medicine residency programs demonstrated no change. CONCLUSION: As the proportion of men entering Ob/Gyn residency programs declines, the number of men entering general Ob/Gyn is declining at an even more dramatic rate.