Over the past century, pituitary surgery has undergone multiple evolutions in surgical technique and technological advancements that have resulted in what practitioners now recognize as modern transsphenoidal surgery (TSS). Although the procedure is now well established in current neurosurgical literature, the historical maze that led to its development continues to be of interest because it allows a better appreciation of the unique contributions by the pioneers of the technique, and of the innovative spirit that continues to fuel neurosurgery. The early events in the history of TSS have already been well documented. This paper therefore summarizes the major early transitions along the timeline, and then further concentrates on some of the more recent advancements in TSS, such as the surgical microscope, fluoroscopy, endoscopy, intraoperative imaging, and frameless guidance. The account of each of these innovations is unique because they were each developed as a response to certain historical needs by the surgeon. An understanding of these more recent contributions, coupled with the early history, provides a more complete perspective on modern TSS.