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Simple Summary: Symptoms such as light-headedness and fainting upon standing can have a large negative impact on the quality of life, especially for people with orthostatic hypotension (blood pressure drop upon or during standing). One treatment option suggested in the clinic is head-up tilted sleeping (HUTS), where the full body is inclined. In this paper we reviewed the available evidence for the use of HUTS. We identified 10 studies focussing on HUTS as a treatment to improve orthostatic tolerance. Unfortunately, the overall evidence was weak, mainly because of the low number of included participants. We also noticed that the studied angles differed as well as the type of measurements to evaluate HUTS. Despite this, the anecdotal evidence suggested that HUTS therapy could slightly improve low standing blood pressure and its associated symptoms. The effects were more marked if higher angles were applied. These results provide some, although weak, evidence favouring HUTS, but the clinical relevance and the tolerability need to be studied further in larger-scale trials. To systematically summarize the evidence of head-up tilt sleeping (HUTS) on orthostatic tolerance, we conducted a systematic, predefined search in PubMed, OVID Embase, Cochrane and Web of Science. We included studies assessing the effect of HUTS on orthostatic tolerance and other cardiovascular measures and rated the quality with the American Academy of Neurology risk of bias tool. We included 10 studies (n = 185) in four groups: orthostatic hypotension (OH; 6 studies, n = 103), vasovagal syncope (1 study, n = 12), nocturnal angina pectoris (1 study, n = 10) and healthy subjects (2 studies, n = 58). HUTS duration varied (1 day–4 months) with variable inclinations (5°–15°). In two of six OH studies, HUTS significantly improved standing systolic blood pressure. Orthostatic tolerance was consistently enhanced in OH studies with higher angles (≥12°), in 2 out of 3 with smaller angles (5°) but also in one studying horizontal sleeping. In vasovagal syncope, HUTS significantly augmented resilience to extreme orthostatic stress. One study was rated as a class II risk of bias, one of Class II/III and eight of Class IV. The evidence favouring HUTS to improve orthostatic tolerance is weak due to variable interventions, populations, small samples and a high risk of bias. Despite this, we found some physiological signs suggesting a beneficial effect. [ABSTRACT FROM AUTHOR]