Background: Lower urinary tract symptoms (LUTS) caused by benign prostatic obstruction (BPO) and bladder tumors may co-exist, especially among elderly patients. Transurethral resection of bladder tumors (TURBT) and endoscopic surgery for benign prostatic obstruction in the same setting are avoided by many surgeons due to concerns for tumor cell seeding and recurrences in the prostatic urethra. Aim: The aim of this study was assess the effect of concomitant TURBT and endoscopic BPO surgery on oncological safety and patient quality of life via systematic review and meta-analysis. Methods: We searched the PubMed, Cochrane Library, EMBASE, Scopus, and Clinicaltrials.gov databases and sources of grey literature published before June 2021 for relevant studies. We performed a random-effects meta-analysis of odds ratios (ORs) or weighted mean differences (WMD) to compare concomitant TURBT and BPO surgery versus TURBT alone in terms of recurrence and progression rates. Accordingly, we undertook multiple subgroups and sensitivity analyses (PROSPERO: CRD42020173363). Results: Three randomized and twelve retrospective observational studies with 2421 participants were included. Across studies with good methodological quality, no statistically significant differences were demonstrated regarding overall bladder tumors recurrence rates between concomitant endoscopic BPO surgery and TURBT versus TURBT alone (OR: 0.81, 95% CI: 0.60–1.09, I2 = 42%). Similarly, no significant differences were observed in recurrences located at the bladder neck and/or prostatic urethra (OR: 1.06, 95% CI: 0.76–1.47, I2 = 0%), time to first recurrence (WMD: −0.2 months, 95% Cl: −2.2–1.8, I2 = 48%), and progression rate (OR: 1.05, 95% CI: 0.67–1.64, I2 = 0%). Subgroup analyses based on tumor grade, number of tumors, and utilization of single-instillation chemotherapy post-TURBT did not detect any significant differences in overall bladder tumor recurrence. The level of evidence was estimated as low for all outcomes. Concomitant surgery improved lower urinary tract symptoms. Conclusion: Concomitant endoscopic BPO surgery and TURBT are oncologically safe and improve LUTS-related quality of life.