Career paths and aspirations were investigated among postgraduate dental trainees on completion of clinical training at Tokyo Dental College between 2006, when clinical residency became mandatory, and 2011. Overall, those finding employment with independent general dental practitioners accounted for the majority (34%), followed by those entering postgraduate courses at the Chiba Hospital (20%), those embarking on a postgraduate clinical specialty course at the Chiba Hospital (16%), and those going on to other universities (7%). At the Chiba Hospital, the number selecting postgraduate courses, residency training (including further residency training or a postgraduate clinical specialty course), or employment with a general dental practitioner was almost the same; however, the number selecting postgraduate courses at the Suidobashi Hospital was low, showing a strong tendency toward becoming a general or clinical practitioner. At the Ichikawa General Hospital, most of the trainees decided to remain at the same school or hospital as postgraduate students or residents, showing an aspiration toward further specialization. The results of the Fisher's exact test showed a significant difference in career paths between the Chiba, Suidobashi, and Ichikawa General Hospitals. Trends among postgraduate dental trainees from this and other schools completing the clinical residency program here and subsequently entering postgraduate courses, further residency training, or a postgraduate clinical specialty course at this school were investigated. No major difference was observed in the percentage of trainees remaining at the same school or entering postgraduate courses between those from this and those from other schools; however, more trainees from other schools selected further residency training, while fewer selected a postgraduate clinical specialty course.