This study investigated the effectiveness of head cooling on cognitive performance after 30 min and 60 min of running in the heat. Ten moderately-trained, non-heat-acclimated, male endurance athletes (mean age: 22 ± 6.6 y; height: 1.78 ± 0.10 m; body-mass: 75.7 ± 15.6 kg; VO_2peak: 51.6 ± 4.31 mL^-1>kg^-1>min) volunteered for this study. Participants performed two experimental trials: head cooling versus no-cooling (within-subjects factor with trial order randomized). For each trial, participants wore a head-cooling cap for 15 min with the cap either cooled to 0°C (HC) or not cooled (22°C; CON). Participants then completed 2 × 30 min running efforts on a treadmill at 70% VO_2peak in hot conditions (35°C, 70% relative humidity), with a 10 min rest between efforts. Working memory was assessed using an operation span (OSPAN) task immediately prior to the 15 min cooling/no-cooling period (22°C, 35% RH) and again after 30 min and 60 min of running in the heat. Numerous physiological variables, including gastrointestinal core temperature (T_c) were assessed over the protocol. Scores for OSPAN were similar between trials, with no interaction effect or main effects for time and trial found (p = 0.58, p = 0.67, p = 0.54, respectively). Forehead temperature following precooling was lower in HC (32.4 ± 1.6°C) compared with CON (34.5 ± 1.1°C) (p = 0.01), however, no differences were seen in T_c, skin temperature, heart rate and ratings of perceived exertion between HC and CON trials at any time point assessed (p > 0.05). In conclusion, despite HC reducing forehead temperature prior to exercise, it did not significantly improve cognitive performance during (half-time break) or after subsequent exercise in hot environmental conditions, compared to a no cooling control.