Salivary cortisol role in response to strong stressors implied in extreme exercises and in sport practice was investigated with the aim to verify the claimed benefits that steers winter swimmers to self-prescribe the trials. Specific biochemical data allow to study a variety of stressors in sports and physical exercises, including extreme ones as winter swimming. Salivary cortisol behavior was examined in winter swimmers trials and canoe, canoe-polo competitions and comparisons of results between days with and without performances were reported. Cortisol circadian rhythm in sedentary subjects was collected as control. All the subjects were selected after anamnestic-clinical checks to evaluate their physiological conditions. The circadian cortisol behavior was reported in days with competitions and trials as well as between these events. Abrupt cortisol concentration changes were detected at the time of the trials and competitions: surprisingly, large increasing and decreasing concentrations were detected in both groups. Moreover, in winter swimmers, cortisol concentration remained fairly elevated in the evening of the trial days. In days without competitions, the usual cortisol circadian rhythm was recovered in sportsmen whereas cortisol concentrations persisted at high levels up to the evening in winter swimmers. The view that an extreme sport-like exercise as the winter swimming may well pose some treats ranging from subclinical aspects up to dismetabolic pathologies and even cardiovascular risks is strengthened by results of cortisol trends, suggesting to check physiological conditions. Results demonstrate that well-being feeling can be in contrast to the claimed improvements of health.