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Endoscopy imaging of the gastrointestinal (GI) tract has evolved tremendously over the last few decades. Key milestones in the development of endoscopy imaging include the use of various dyes for chromoendoscopy, the application of optical magnification in endoscopy, the introduction of high-definition image capturing and display technology and the application of altered illuminating light to achieve vascular and surface enhancement. Aims of this review paper are to summarize the development and evolution of modern endoscopy imaging and in particular, imaged-enhanced endoscopy (IEE), to promote appropriate usage, and to guide future development of good endoscopy practice. A search of PubMed database was performed to identify articles related to IEE of the GI tract. Where appropriate, landmark trials and high-quality meta-analyses and systematic reviews were used in the discussion. In this review, the developments and evolutions in endoscopy imaging and in particular, IEE, were summarized into discernible eras and the literature evidence with regard to the strengths and weaknesses in term of their detection and characterization capability in each of these eras were discussed. It is in the authors’ opinion that IEE is capable of fairly good detection and accurate characterization of various GI lesions but such benefits may not be readily reaped by those who are new in the field of luminal endoscopy. Exposure and training in making confident diagnoses using these endoscopy imaging technologies are required in tandem with these new developments in order to fully embrace and adopt the benefits.