Beginning with a nascent few programs a hundred years ago, to over 155 separate residency programs today, there has been an evolution of residency program structure, content, and pedagogy that has served to educate new doctors into trained specialists. The purpose of this chapter is to review the changes and content for orthopaedic surgery and to document the changes in the structure and practice of orthopaedic education with a particular focus on how orthopaedic surgery has been taught within the residency program. What were the structural changes that took place over time? With advances in the field, how did the content change over time? What methods were used to provide education of residents? By viewing orthopaedic surgery residency programs in this longitudinal fashion, it potentially provides us a road map in providing future direction to residency programs.