Multiple supernumerary teeth are usually associated with various syndromes, but they are relatively uncommon as an isolated dental anomaly. The presence of multiple supplemental premolars in all four quadrants and especially in the maxilla is rare. This report presents a unique case of multiple supplemental premolars in all four quadrants that were distributed unevenly (two erupted; five unerupted). A series of radiographs taken over four years demonstrated further sequential developing bilateral supplemental premolars in the maxilla, where they are considered the rarest. Appropriate management and the importance of regular radiographic monitoring of such cases are briefly reviewed.