Background/Objectives: Skene’s gland malignancies are extremely rare tumors of the female paraurethral region, known almost exclusively from case reports and small case series. Their diagnosis is often delayed because symptoms are nonspecific and may mimic benign periurethral disorders, urethral diverticula, primary urethral carcinoma or anterior vaginal wall tumors. This narrative review focuses on the role of imaging, particularly pelvic magnetic resonance imaging (MRI), in the diagnosis, differential diagnosis, staging and treatment planning of Skene’s gland malignancies, distinguishing evidence from confirmed Skene’s gland cases from evidence extrapolated from female urethral carcinoma. Methods: PubMed/MEDLINE, Scopus and Web of Science were searched on 27 September 2026 (publication years 2015–2026) and supplemented by reference-list screening; an explicit case definition was applied. Results: Of 191 records (93 after de-duplication), 17 reports of Skene’s gland malignancy were included (15 case reports or series and 2 systematic reviews); fewer than thirty cases have been published overall. Patients were mostly postmenopausal (median age about 70 years, range 45–91), presenting with an asymptomatic periurethral nodule, hematuria or vaginal bleeding, or lower urinary tract symptoms; no uniform staging system has been applied. Most tumors were prostatic-type adenocarcinomas treated by local excision alone; radiotherapy, chemotherapy or androgen deprivation were used mainly for nodal, metastatic or recurrent disease. After examination, ultrasonography can detect and characterize a paraurethral mass, whereas MRI best defines tumor epicenter, urethral, periurethral and anterior vaginal wall involvement and regional spread, and should precede cystourethroscopy and biopsy; CT and PET/CT are complementary for systemic staging. No single immunohistochemical marker establishes Skene’s gland origin. Conclusions: MRI is central to localizing and staging suspected Skene’s gland malignancy and thus to guiding biopsy and the choice between local excision and radical surgery, but most imaging recommendations are extrapolated from female urethral carcinoma and require validation in pooled multicenter data.