High-modulus asphalt concrete has numerous advantages in comparison to conventional asphalt concrete, including increased resistance to permanent deformations and increased pavement fatigue life. However, previous studies have shown that the construction of road pavements with High Modulus Asphalt Concrete (HMAC) may significantly increase the risk of low-temperature cracking. Those observations were the motivation for the research presented in this paper. Four test sections with HMAC used in base and binder courses were evaluated in the study. Field investigations of the number of low-temperature cracks were performed over several years. It was established that the number of new low-temperature cracks is susceptible to many random factors, and the statistical term “reversion to the mean” should be considered. A new factor named Increase in Cracking Index was developed to analyze the resistance of pavement to low-temperature cracking. For all the considered field sections, samples were cut from each asphalt layer, and Thermal Stress Restrained Specimen Tests were performed in the laboratory. Correlations of temperature at failure and cryogenic stresses with the cracking intensity observed in the field were analyzed. The paper provides practical suggestions for pavement designers. When the use of high modulus asphalt concrete is planned for binder course and asphalt base, which may result in lower resistance to low-temperature cracking of pavement than in the case of conventional asphalt concrete, it is advisable to apply a wearing course with improved resistance to low-temperature cracking. Such an approach may compensate for the adverse effects of usage of high modulus asphalt concrete.