To investigate the influence of the initial clinical presentation (symptomatic vs. asymptomatic) on histopathological tumor features in patients with upper tract urothelial carcinoma (UTUC). We conducted a single-center, cross-sectional, and retrospective study that enrolled 72 adults with primary UTUC who underwent radical nephroureterectomy at our institution over a period of 4 years (April 2019-April 2023). Symptomatic patients exhibited significantly higher frequencies of high-grade UTUC (73.6% vs. 36.8%, p = 0.006), ≥ T2 stage UTUC (60.4% vs. 26.3%, p = 0.007), and larger tumor sizes (median 5 vs. 4cm, p = 0.015) compared to asymptomatic patients. Multiple regression analyses demonstrated significant associations between symptomatic presentation and the presence of high-grade UTUC (OR 6.35, 95% CI 1.81-22.27, p = 0.004), ≥ T2 stage UTUC (OR 5.98, 95% CI 1.62-22.08, p = 0.007), and larger tumor size (B 3.14, 95% CI 0.62-5.66, p = 0.015). A subset of patients with hematuria was separately analyzed to assess the influence of hematuria severity (gross vs. microscopic) on UTUC characteristics. Patients with gross hematuria exhibited significantly higher frequencies of high-grade UTUC (72.9% vs. 33.3%, p = 0.048) and ≥ T2 stage UTUC (58.3% vs. 22.2%, p = 0.001). Multiple regression analyses showed significant associations between gross hematuria and the presence of high-grade UTUC (OR 6.34, 95% CI 1.15-34.95, p = 0.034) and ≥ T2 stage UTUC (OR 6.54, 95% CI 1.11-38.93, p = 0.039). Initial symptomatic presentation was independently associated with adverse histopathological UTUC characteristics, potentially attributed to earlier detection of UTUC in asymptomatic patients, before the onset of symptoms.