The excess heat accumulated during exercise can lead to stress-induced fatigue, possibly impairing athletic performance. Various precooling techniques have been applied to enhance thermal comfort, reduce perception of effort, and improve endurance. In this randomized crossover study, twelve male amateur middle-distance runners (age: 33.69 ± 5.9 years; body mass: 71.9 ± 4.4 kg; height: 178.4 ± 5.6 cm; O2 peak: 63.3 ± 5.6 mL·min-1·kg-1) wore a facial cooling mask before a time-to-exhaustion (TTE) test on a treadmill, under cryostimulation or control conditions. The running performance comprised also two constant load trials, one conducted before and another after wearing the mask, both performed at the velocity of the first ventilatory threshold. Under cryostimulation condition, the TTE was 13% higher than the control condition (p = 0.0049; d = -0.19) with a significant main effect of time for both ratings of perceived exertion (F1, 22 = 50.10; p < 0.0001; η2p = 0.69) and heart rate (F1, 22 = 31.53; p < 0.0001; η2p = 0.59). A significant interaction “condition × time” was found for facial skin temperature (F2, 44 = 36.93; p < 0.0001; η2p = 0.63) and for heart rate during the constant load trial after wearing the mask (F1, 22 = 5.90; p = 0.0238; η2p = 0.21). The localized cryostimulation provided by the mask lowered the skin temperature on the face, potentially mitigating the negative effects of heat stress during running. Incorporating the cryo-facial mask as part of a pre-exercise routine for runners may offer a practical and convenient method to optimize performance and enhance overall training outcomes.