Background: In football, annual age-group categorization leads to relative age effects (RAEs) in talent development. Given such trends, relative age may also associate with market values. This study analyzed the relationship between RAEs and market values of youth players. Methods: Age category, birthdate, and market values of 11,738 youth male football players were obtained from the “transfermarkt.de” database, which delivers a good proxy for real market values. RAEs were calculated using odds ratios (OR) with 95% confidence intervals (95%CI). Results: Significant RAEs were found across all age-groups (p < 0.05). The largest RAEs occurred in U18 players (Q1 [relatively older] v Q4 [relatively younger] OR = 3.1) ORs decreased with age category, i.e., U19 (2.7), U20 (2.6), U21 (2.4), U22 (2.2), and U23 (1.8). At U19s, Q1 players were associated with significantly higher market values than Q4 players. However, by U21, U22, and U23 RAEs were inversed, with correspondingly higher market values for Q4 players apparent. While large typical RAEs for all playing positions was observed in younger age categories (U18–U20), inversed RAEs were only evident for defenders (small-medium) and for strikers (medium-large) in U21–U23 (not goalkeepers and midfielders). Conclusions: Assuming an equal distribution of football talent exists across annual cohorts, results indicate the selection and market value of young professional players is dynamic. Findings suggest a potential biased selection, and undervaluing of Q4 players in younger age groups, as their representation and market value increased over time. By contrast, the changing representations and market values of Q1 players suggest initial overvaluing in performance and monetary terms. Therefore, this inefficient talent selection and the accompanying waste of money should be improved.