Introduction: Penile inversion vaginoplasty (PIV) remains the gold standard technique for vaginoplasty, a gender-affirming feminizing surgery, but has been associated with urinary complications; however, there is little literature synthesizing urinary complications after PIV surgery, and there is a need to compile these complications to counsel patients pre- and postoperatively on managing surgical expectations. In this systematic review, we summarize the prevalence of urinary complications following PIV. Methods: We searched the MEDLINE, EMBASE, CINAHL, and Scopus databases in July 2020. The primary outcome was the prevalence of urinary and surgical complications in patients after penile inversion vaginoplasty. Pooled prevalence was determined from extrapolated data. ROBINS-I tool was used to assess study quality. The study was prospectively registered on PROSPERO (CRD42020204139). Results: Of 843 unique records, 27 articles were pooled for synthesis, with 3388 patients in total. Overall patient satisfaction ranged from 80–100%. The most common urological complications included poor/splayed stream (11.7%, 95% confidence interval [CI] 5.7–19.3), meatal stenosis (6.9%, 95% CI 2.7–12.7), and irritative symptoms (frequency, urgency, nocturia) (11.5%, 95% CI 2.6–25.1). Other urinary complications included retention requiring catheterization (5.1%, 95% CI 0.3–13.8), incontinence (8.7%, 95% CI 3.4–15.6), urethral stricture (4.6%, 95% CI 1.2–9.8), and urinary tract infection (5.6%, 95% CI 2.7–9.4). Most pooled studies had moderate risk of bias. Conclusions: The available evidence suggests that there is a low prevalence of urinary complications following PIV. Overall, there is a need for standardization of data in transgender surgical care to better understand surgical outcomes and improve postoperative management.