Transposition is a unique and extreme form of ectopic eruption where a tooth develops and erupts in a position, normally occupied by an adjacent tooth. Generally, three treatment options are available when the maxillary canine and first premolar are transposed. In the first treatment option, the transposed position of the teeth can be maintained such that the first premolar is moved to the position of the canine. Second, extraction of the maxillary first premolar can be considered. Third, the position of the transposed teeth can be corrected such that their normal positions in the arch are restored. Factors that should be considered in treatment modality decision include function, occlusion, periodontal support, treatment time, patient cooperation, and esthetic demands. This report describes cases of maxillary canine-premolar transposition treated with each of the three aforementioned treatment options. In the first case, transposed teeth were arranged in their transposed position. The second case was an extraction case. In the third case, orthodontic treatment and surgical repositioning were conducted.