Though there are exhaustive data about participation, performance trends, and sex differences in performance in different running disciplines and races, no study has analyzed these trends in stair climbing and tower running. The aim of the present study was therefore to investigate these trends in tower running. The data, consisting of 28,203 observations from 24,007 climbers between 2014 and 2019, were analyzed. The effects of sex and age, together with the tower characteristics (i.e., stairs and floors), were examined through a multivariable statistical model with random effects on intercept, at climber’s level, accounting for repeated measurements. Men were faster than women in each age group (p < 0.001 for ages ≤69 years, p = 0.003 for ages > 69 years), and the difference in performance stayed around 0.20 km/h, with a minimum of 0.17 at the oldest age. However, women were able to outperform men in specific situations: (i) in smaller buildings (<600 stairs), for ages between 30 and 59 years and >69 years; (ii) in higher buildings (>2200 stairs), for age groups <20 years and 60–69 years; and (iii) in buildings with 1600–2200 stairs, for ages >69 years. In summary, men were faster than women in this specific running discipline; however, women were able to outperform men in very specific situations (i.e., specific age groups and specific numbers of stairs).