Purpose: This study examines the evolution of treatments for oesophageal diseases since the 1923 edition of Bailey & Love’s Short Practice of Surgery, comparing historical practices with current standards to highlight transformative advancements in surgical and medical care. Methodology: Treatments described in the 1923 textbook were reviewed and categorised by condition type (e.g., congenital, neoplastic, inflammatory, traumatic). These approaches were then compared to contemporary standards, emphasising diagnostic modalities, therapeutic strategies, and outcomes. The study also contextualises historical practices within the technological and scientific constraints of the era. Results: Over the last century, the management of oesophageal diseases has seen significant evolution. Historical reliance on invasive and rudimentary methods has been supplanted by precise diagnostics, minimally invasive techniques, and evidence-based medical therapies. Key advancements have improved patient safety, reduced morbidity, and enhanced overall outcomes. These transformations reflect broader trends in surgical innovation, integration of endoscopic technologies, and pharmacological breakthroughs. Conclusion: The transition from early 20th-century practices to modern oesophageal care illustrates the remarkable progress in surgical education, research, and clinical application. This retrospective analysis not only highlights the innovations that have shaped current practices but also underscores the importance of continued advancement in patient care.