White-coat uncontrolled hypertension (WUCH) and masked uncontrolled hypertension (MUCH) are common in the elderly. The prognostic role of these hypertension phenotypes is not completely defined in this subpopulation. Our aim is to evaluate the long-term prognostic role of WUCH and MUCH in treated elderly hypertensives. Observational study conducted on 120 consecutive treated elderly hypertensives. Patients were assessed on a first clinical visit in 2006. Subsequently, such patients or their relatives have been recalled after 10 years to evaluate the survival rates. Main inclusion criteria at baseline: age ≥ 65 years, a previous diagnosis of essential hypertension, a valid 24-h ambulatory blood pressure monitoring (ABPM). All participants received anti-hypertensive drugs during the 10-year period and we considered 10-year mortality for the analysis. General characteristics at baseline: mean age was 71.2 ± 5.3 years; females were 53.3%; 15.1% of patients had sustained controlled hypertension (SCH), 35.8% had WUCH, 10.8% had MUCH and 38.3% had sustained uncontrolled hypertension (SUCH). Thirty-two patients (26.7%) died during the 10-year period. Deceased patients were older, had lower treatment intensity, HDLc levels and eGFR than survivors. After adjusting for these covariates, MUCH (HR 12.30, p < 0.001) and SUCH (HR 4.84, p = 0.007) were associated with higher risk of death, compared to SCH, while no relationship emerged with WUCH (HR 1.58, p = 0.455). In our real-life study on treated elderly hypertensives, MUCH was associated with higher risk of death, compared to SCH and SUCH, while WUCH was not. ABPM is a key tool to improve management and therefore prognosis in this subpopulation.