Asynclitism, the most feared malposition of the fetal head during labor, still represents to date an unresolved field of interest, remaining one of the most common causes of prolonged or obstructed labor, dystocia, assisted delivery, and cesarean section. Traditionally asynclitism is diagnosed by vaginal examination, which is, however, burdened by a high grade of bias. On the contrary, the recent scientific evidence highly suggests the use of intrapartum ultrasonography, which would be more accurate and reliable when compared to the vaginal examination for malposition assessment. The early detection and characterization of asynclitism by intrapartum ultrasound would become a valid tool for intrapartum evaluation. In this way, it will be possible for physicians to opt for the safest way of delivery according to an accurate definition of the fetal head position and station, avoiding unnecessary operative procedures and medication while improving fetal and maternal outcomes. This review re-evaluated the literature of the last 30 years on asynclitism, focusing on the progressive imposition of ultrasound as an intrapartum diagnostic tool. All the evidence emerging from the literature is presented and evaluated from our point of view, describing the most employed technique and considering the future implication of the progressive worldwide consolidation of asynclitism and ultrasound.