Paratesticular soft tissue tumours are remarkably rare entities, with malignant subtypes accounting for approximately 30%. Due to the paucity of cases, a consensus on the best treatment has not yet been reached, presenting a diagnostic and therapeutic challenge for clinicians. Although rare, three such cases presented to the care of our institution serving a population of approximately 400,000 in the space of 13 months. These were three gentlemen, aged 54, 82 and 86 years old, presenting with left sided testicular swellings. Ultrasound in each case confirmed an extratesticular mass. Only the second gentleman complained of associated pain, however he had experienced scrotal trauma in the preceding weeks. Only one patient had suspicions of metastatic disease, with a 9 mm pulmonary nodule on computed tomography. All patients underwent a radical inguinal orchidectomy with high ligation of the spermatic cord, in keeping with best accepted guidelines. Histology confirmed a well-differentiated liposarcoma, a dedifferentiated liposarcoma and a leiomyosarcoma respectively, all high grade. One gentleman returned to theatre for re-excision of margins. Our case series emphasises the need for full multidisciplinary team specialist sarcoma input, as well as radical resection with judicious margins in order to reduce the risk of local recurrence, in the treatment of these rare tumours.