A male patient about 45 years old came to my private clinic "The Dental Aid", Dhanmondi, Dhaka, Bangladesh last year (February 2016) with the complaint of pain at right palatal premolar region. On clinical examination we found the absence of upper left 2nd premolar from the series of dentition but on the right side premolars are present. The oral mucosa was intact and normal in color. There was no caries, dental pocket or any other pathology in the teeth of both jaws. On palpation we found soft area on the right palatal side at the premolar area. We took intraoral peri-apical radiograph and found impacted left 2nd premolar whose crown was encircled by radiolucent area at the palatal side. Here, we present a rare case of transmigrated and impacted left 2nd maxillary premolar associated with dentigerous cyst. The cyst was successfully treated under general anaesthesia by enucleation along with extraction of the involved maxillary transposed and impacted left second premolar.