A pilot study in the Oslo region of Norway followed 90 adult patients with type 1 or type 2 diabetes from December 2019 to January 2021 with annual screening for diabetic retinopathy (DR) using fundus photographs and optical coherence tomography. At the beginning, 27.8% of patients had DR, of which 6.7% had sight-threatening DR (VTDR). Over three years, 24.7% of patients developed or progressed to DR, while 4% developed VTDR. Duration of diabetes (hazard ratio 1.07; 95% CI 1.02–1.12) and urinary albumin to creatinine ratio (hazard ratio 1.03; 95% CI 1.01–1.06) were significantly associated with DR progression. The severity of DR was assessed according to the International Scale, and diabetic macular edema was identified from OCT findings. 13.3% of patients were lost to follow-up, mainly due to the COVID-19 pandemic. Most patients had stable DR, with duration of diabetes and albuminuria predicting progression, supporting risk-stratified screening with extended intervals in low-risk patients.