Background: The association between orthostatic hypotension and supine hypertension (Hypo–Hyper) has been reported in previous studies on selected populations. The present longitudinal study aimed to characterize the haemodynamic patterns, comorbidity, prognostic implications and eventual effect of therapy in patients with the Hypo–Hyper pattern. Methods: Ambulatory blood pressure monitoring (AMAP) and clinical evaluation were performed on 615 consecutive patients recruited from the Hypertension Clinics of five Italian Hospitals: 34 patents were identified as Hypo–Hyper, and underwent 10‐month follow‐up. Results: The incidence of the Hypo–Hyper pattern was 5.5% in the hypertensives studied. Hypo–Hyper was more frequent in the elderly (mean age 58 years), and the affected population exhibited different kinds of underlying pathologies. Multivariate analysis showed no association between antihypertensive treatment and Hypo–Hyper pattern. Patients with AMAP features of higher blood pressure values at night‐time than at daytime displayed higher rates of myocardial hypertrophy and pacemaker implantation during the follow‐up. Conclusions: Although the study design did not aim to identify any pathophysiological mechanism for Hypo–Hyper pattern, these first data show that the Hypo–Hyper association is the effect of a particular subtype of hypertension, with significantly different prognostic implications.