(1) To compare fractal dimension (FD) from periapical radiographs with FD from panoramic radiographs; (2) to correlate FD with cortical thickness and morphology; and (3) to correlate FD with a reported history of osteoporotic fractures. Information on fracture and smoking history was obtained by a telephone interview with 281 elderly (>60 years of age) patients who had periapical and panoramic radiographs exposed on the same date. FD was measured in several locations on both types of radiograph. Mandibular cortical thickness and morphology were obtained from the panoramic radiograph. FD measured in the mandible was lower than FD in the maxilla. Same-jaw measurements had a higher correlation than same-side measurements. FD measured on panoramic radiographs was lower than FD from periapical radiographs. There was a negative correlation between cortical thickness and FD. FD was higher in subjects with more mandibular cortical porosities and resorption. The mean panoramic FD from subjects with a history of osteoporotic fractures was significantly higher, after adjusting for smoking, gender, age, height and weight. FD measured on panoramic radiographs is lower than FD measured on periapical radiographs. FD is higher in both types of radiograph in subjects with a thinner, severely eroded mandibular cortex and a history of osteoporotic fractures. This study confirms other reports that FD increases when bone mass decreases. In addition, it suggests that panoramic radiographs can be used as a possible alternative for the measurement of FD to periapical radiographs.