The aim of this observational study was to evaluate screening and progression of diabetic retinopathy during pregnancy in women with pregestational diabetes attending five antenatal centres along the Irish Atlantic seaboard. An adequate frequency of screening was defined as at least two retinal evaluations in separate trimesters. Progression was defined as at least one stage of deterioration of diabetic retinopathy and/or development of diabetic macular edema on at least one eye. Women with pregestational diabetes who delivered after 22 gestational weeks (n = 307) were included. In total, 185 (60.3%) had an adequate number of retinal examinations. Attendance at prepregnancy care was associated with receiving adequate screening (odds ratio 6.23; CI 3.39-11.46 (P < 0.001)). Among those who received adequate evaluations (n = 185), 48 (25.9%) had retinopathy progression. Increasing booking systolic blood pressure (OR 1.03, CI 1.01-1.06, P = 0.02) and greater drop in HbA1c between first and third trimesters of pregnancy (OR 2.05, CI 1.09-3.87, P = 0.03) significantly increased the odds of progression. A significant proportion of women continue to demonstrate retinopathy progression during pregnancy. This study highlights the role of prepregnancy care and the importance of close monitoring during pregnancy and identifies those patients at the highest risk for retinopathy progression.