Canada and Australia share similar cultural origins and current multicultural societies and demographics but there are differences in climate and sporting pursuits. Surgeons and surgeon teachers similarly share many of the same challenges, but the health care and health-care education systems differ in significant ways. The objective of this review is to detail the different postgraduate surgical training programs with a focus on general surgery and how the programs of each country may benefit from appreciating the experiences of the other. The major differences relate to entry requirements, the role of universities in governance of training, mandatory skills courses in early training, the accreditation process, remuneration for surgical teachers and the impact of private practice. Many of the differences are culturally entrenched in their respective medical systems and unlikely to change substantially. Direct entry into specialty training without an internship per se is now firmly established in Canada just as delayed entry after internship is mandated by the Australian Medical Board. Both recognize the importance of establishing goals and objectives, modular curricular and the emerging role of online educational resources and how these may impact on assessments. The Royal Australasian College of Surgeons is unlikely to cede much responsibility to the universities but alternative academic models are emerging. Private health care in the two countries differs, but there are increasing opportunities for training in the private sector in Australia. In spite of the differences, both provide excellent health care and surgical training opportunities in an environment with significant fiscal, technological and societal challenges.