Oesophagitis dissecans superficialis (ODS) is a very rare, benign and poorly understood flat oesophageal lesion with an incidence of 0.03%. In this case study, we look at unique endoscopic images of a 59-year-old male with seven presentations for food bolus impaction over the course of 2 years diagnosed with ODS after multiple oesophageal biopsies. The clinical course, multifactorial management and unique endoscopic findings are presented to understand the progression and spectrum of this rare disease. In addition, we explore the role of histopathology and adequate oesophageal sampling required for oesophageal lesions with suspected ODS.