Background and Objectives: We examined the possible trend in the age of peak performance in elite endurance athletes according to sex, continent of athletes’ national citizenship, and ranking position. Since performance is a multifactorial trait, this information can be used to guide the long-term training and to plan the strategies related to the selection process of athletes. Materials and methods: Information of 1852 professional athletes, classified as top 20 performance of each year in marathon and half-marathon events between 1997 and 2020 were considered. Analysis of variance was computed to test differences in age between sex, continent, and rank position. Results: A significant difference between groups in the mean age of peak performance was observed (F (3, 1884) = 42,31; p < 0.001). For both sexes, half-marathoners were younger than marathoners (male, 25.6 ± 3.6 years vs. 28.0 ± 3.9 years; female, 27.5 ± 4.4 years vs. 28.4 ± 4.1). Female half-marathoners in 2004 presented the highest mean age (31.1 ± 4.8 years) compared to their peers in the years 1997, 2001, 2018 and 2019; among male half-marathoners, those in 1999 presented the highest mean age when compared to 2011, 2018, and 2019. Differences between the continents of athletes’ national citizenship were observed (F (4, 1884) = 62,85,601; p < 0,001). Asian runners presented the lowest mean age (26.5 ± 3.7 years), while their European peers presented the highest (31.1 ± 3.9 years). No significant interaction between sex and ranking position was verified. Differences were observed between sexes for categories “4th–10th positions” and “11th–20th” (F (1, 1879) = 23,114; p < 0.001). Conclusions: Over the last two decades, no clear trend was observed in the changes in the age of peak performance among endurance athletes of both sexes, but, in general, female half-marathoners tended to be significantly older than their male peers.