A high-order pregnancy is always a challenge not only for the couple but also for the obstetrician, the pediatricians, the midwives, and the whole stuff of an obstetric clinic. The breakthroughs of infertility treatments have made more couples to postpone the birth of their children until they feel professionally and financially safe, many times after the age of 40. The advanced age of the mother puts extra pressure to the clinician for immediate success, leading to a rise of high-order pregnancies until the introduction of regulations and laws in many countries. The cost of a quadruplet and quintuplet pregnancy can be unbearable, not only financially but also psychologically. The management of such a pregnancy is also challenging since its beginning and to the end. Modern techniques and methods can also be difficult to be implemented on a quadruplet of quintuplet pregnancy because of the fear of losing four or five embryos at once. At the same time, the limited number of cases makes it almost impossible for studies to be made and guidelines to be established for most of the cases.