As a third of people with diabetes mellitus (DM) will suffer the microvascular complications of diabetic retinopathy (DR) and therapeutic options can effectively prevent visual impairment, systematic screening has substantially reduced disease burden in developed countries. In an effort to tackle the rising incidence of DM, screening programmes have modernized in synchrony with technical and infrastructural advancements. Patient evaluation has shifted from face-to-face ophthalmologist-based review delivered through community grassroots to asynchronous store-and-forward modern telemedicine platforms commissioned on a nationwide scale. First pioneered with primitive 35-mm slide film retinal photography, the last decade has seen an emergence of high resolution and widefield imaging devices, which may reveal extents of DR indiscernible to the clinician but with implications of potential earlier identification. Similar progress has been seen in image analysis approaches – automated image analysis of retinal photographs of DR has evolved from qualitative feature detection to rules-based algorithms to autonomous artificial intelligence-powered classification. Such models have, relatively rapidly, been validated and are now receiving approval from health regulation authorities with deployment into the clinical sphere. In this review, we chart the evolution of global DR screening programmes since their inception highlighting major milestones in healthcare infrastructure, telemedicine approaches and imaging devices that have shaped the robust and effective frameworks recognised today. We also provide an outlook for the future of DR screening in the context of recent technological advancements with respect to their limitations in current times.© 2020 Huemer et al.