Objectives: To assess for predictors of outcome in patients presenting with acute urinary retention (AUR). Methods: A study was performed in our unit to evaluate trial without catheter (TWOC) and successive management. We assessed for predictors of surgical or medical management, which included: age, volume drained at time of catheterisation, cause of retention, serum creatinine, success of trial of voiding, co-morbidities, prostate-specific antigen (PSA) and prostate size on digital rectal examination (DRE). Results: 72 men were entered into the study over an 18-month period: 27 had a successful first TWOC, 20 patients had a second TWOC, and 6 were successful. In total, 31 of the 33 patients with a successful TWOC remained on α-blockers without a further episode of AUR within a minimum of 6 months’ follow-up. Patients failing TWOC were managed by transurethral resection of the prostate (n = 22), long-term catheterisation (n = 15) or prostatic stents (n = 3), and 1 patient died prior to intervention. Three predictors were significant on multivariate analysis: PSA (>2.9 ng/ml), prostate size on DRE (large) and volume drained at time of catheterisation (≥1,000 ml). Conclusion: Patients with elevated PSA (>2.9 ng/ml), a large prostate size on DRE and a volume drained at time of catheterisation >1,000 ml are best managed by surgical intervention, while those with volumes drained at time of catheterisation of <1,000 ml, a PSA ≤2.9 ng/ml, and moderate to small prostate on DRE may be managed medically.