Benign uterine disorders, including uterine fibroids (UF) and adenomyosis (AM), can impact the life quality and fertility of women of reproductive age. Transvaginal ultrasound (TVUS) has long been used for their early identification, but its combined use with elastography seems to improve diagnostic accuracy of UF and AM. Thus, a prospective pilot study was conducted on 79 patients who underwent hysterectomy (25 microscopically diagnosed with AM and 53 with UF), with the aim of assessing the ability of TVUS combined with strain ratio elastography (SE) to accurately diagnose and distinguish UF and AM. Significantly higher mean and maximal strain ratio (SR) values were identified for patients with histologically confirmed AM as opposed to those with UF (p < 0.001). Diagnostic sensitivity and specificity, calculated in comparison with histology results, were higher for UF than AM. Receiver operating characteristic (ROC) analysis was applied between the two study groups, revealing cutoff values of 7.71 for mean SR and 8.91 for maximal SR, respectively, with good sensitivity and specificity parameters (100% and 96.23%; 96% and 96.23%). Our results support the use of TVUS in combination with SE for the positive and differential diagnosis of UF and AM, through identification of their particular tissue stiffness features.