Objectives: This study investigated the visual search behaviour of optometrists and fellowship-trained ophthalmologists when screening for diabetic retinopathy in retinal photographs. Methods: Participants assessed and graded retinal photographs on a computer screen while a Gazepoint GP3 HD eye tracker recorded their eye movements. Areas of interest were derived from the raw data using Hidden Markov modelling. Fixation strings were extracted by matching raw fixation data to areas of interest and resolving ambiguities with graph search algorithms. Fixation strings were clustered using Affinity Propagation to determine search behaviours characteristic of the correct and incorrect response groups. Results: A total of 23 participants (15 optometrists and 8 ophthalmologists) completed the grading task, with each assessing 20 images. Visual search behaviour differed between correct and incorrect responses, with data suggesting correct responses followed a visual search strategy incorporating the optic disc, macula, superior arcade, and inferior arcade as areas of interest. Data from incorrect responses suggest search behaviour driven by saliency or a search pattern unrelated to anatomical landmarks. Referable diabetic retinopathy was correctly identified in 86% of cases. Grader accuracy was 64.8% with good inter-grader agreement (α = 0.818). Conclusions: Our study suggests that a structured visual search strategy is correlated with higher accuracy when assessing retinal photographs for diabetic retinopathy. Referable diabetic retinopathy is detected at high rates; however, there is disagreement between clinicians when determining a precise severity grade.