Hypertension and arterial stiffening are independent predictors of cardiovascular mortality. Flavonoids may exert some vascular protection. We investigated the effects of black tea on blood pressure (BP) and wave reflections before and after fat load in hypertensives. According to a randomized, double-blind, controlled, cross-over design, 19 patients were assigned to consume black tea (129 mg flavonoids) or placebo twice a day for eight days (13 day wash-out period). Digital volume pulse and BP were measured before and 1, 2, 3 and 4 h after tea consumption. Measurements were performed in a fasted state and after a fat load. Compared to placebo, reflection index and stiffness index decreased after tea consumption (p < 0.0001). Fat challenge increased wave reflection, which was counteracted by tea consumption (p < 0.0001). Black tea decreased systolic and diastolic BP (−3.2 mmHg, p < 0.005 and −2.6 mmHg, p < 0.0001; respectively) and prevented BP increase after a fat load (p < 0.0001). Black tea consumption lowers wave reflections and BP in the fasting state, and during the challenging haemodynamic conditions after a fat load in hypertensives. Considering lipemia-induced impairment of arterial function may occur frequently during the day, our findings suggest regular consumption of black tea may be relevant for cardiovascular protection.