We report a case of multifocal choroidal melanoma in the same eye, separated in presentation by 20 years. A 57-year-old Caucasian male initially presented with a choroidal melanoma of the right eye that was treated with transpupillary thermotherapy. Due to recurrence, the patient underwent proton beam therapy with subsequent tumor regression. A second small choroidal lesion was noted in the right eye during his surveillance examinations that was closely monitored and demonstrated stable dimensions and features suggestive of a choroidal nevus. Twenty years after his first presentation, the second lesion exhibited accelerated growth with imaging studies indicative of transformation to a distinct choroidal melanoma. The patient underwent a second globe salvage treatment of proton beam therapy. We describe the clinical course, radiographic, and imaging findings of this rare choroidal melanoma.