Diabetes mellitus (DM), a disorder rapidly growing in prevalence, is linked to the retinal microvasculature complication diabetic retinopathy (DR). As one of the leading global causes of vision impairment and loss, imaging techniques to detect and monitor DR must continue to improve in order to address this growing burden. Optical coherence tomography angiography (OCTA) is a nascent imaging modality that generates three-dimensional visualizations of the retinal and choroidal microvasculature. Compared to fluorescein angiography, the gold-standard imaging modality for retinal vessels, OCTA offers the advantages of being non-invasive, quick, and able to resolve the multiple plexuses within the retina. Quantitative OCTA studies have explored parameters such as vessel density (VD), foveal avascular zone (FAZ), acircularity index, vessel tortuosity (VT), and fractal dimension (FD) amongst DR patients. This review synthesizes the main trends emerging from quantitative OCTA-based studies of DR and interrogates them within the context of DR pathophysiology. We offer a glimpse into how analysis techniques have shifted in the years since OCTA came into existence, while speculating on its future role in clinical practice.