Vascular bypass surgery takes a significant place in the treatment of vascular disease. According to various assessments, this type of surgery is associated with almost 20 % of all vascular surgery episodes (up to 23 % according to the Federal Neurosurgical Center of Novosibirsk). Even though the problem of using of vascular grafts is obvious and natural, many problems associated with them are not still elucidated. From the mechanics’ point of view, a vascular bypass is a converging or diverging tee, and the functioning of such structures still does not have strict mathematical formulations and proofs in the general case, which forces many researchers to solve specific engineering problems associated with shunting. Mathematical modeling, which is the gold standard for virtual simulations of industrial and medical problems, faces great difficulties and limitations in solving problems for vascular bypasses. Complications in the treatment of the vascular disease may follow the difficulties in mathematical modeling, and the price can be a cardiac arrest or a stroke. This work is devoted to the main aspects of the medical application of vascular bypasses and their functioning as a mechanical system, as well the mathematical aspects of their possible setup.