Background: To identify differences in radiographic outcomes in weight-bearing lateral X-ray to predict the probability of ulceration in patients with midfoot Charcot neuroarthropathy (CN) differentiated by lateral and medial column deformities. Methods: Thirty-five patients who suffered from CN midfoot deformity participated in this 1 year prospective study in a specialized diabetic foot unit. Lateral talar-first metatarsal angle, calcaneal pitch, and cuboid height were performed by digital radiographs in the weight-bearing lateral view. Patients were followed up for 1 year or until an ulcer ulceration event occurred in the midfoot region. Results: ROC analyses showed that all patients with medial pattern deformity that developed a midfoot ulcer had a lateral talar-first metatarsal angle greater (negative) than −27.5 degrees (°). All patients with lateral pattern deformity that developed a midfoot ulcer had a calcaneal pitch greater (more negative) than −5° and a cuboid height greater (more negative) than −1.5°. Conclusions: Lateral talar-first metatarsal angle was the greatest predictor of midfoot ulceration, with greater than −27.5° measurement correlating with ulceration occurrence in patients with medial deformity. Calcaneal pitch and cuboid height were the greatest predictors of midfoot ulceration with greater than −5 and −1.5°, respectively in patients with CN lateral deformity.