Purpose: To investigate the relationship of field-derived power and physical performance parameters with competition success in road cycling climbing specialists of age-related categories and to explore cross-sectional differences between high-ranked (HIGHR) climbing specialists of each category. Methods: Fifty-three male climbers participated in this study (junior [JUN], n = 15; under 23 [U23], n = 21; professional [PRO], n = 17). Training and racing data collected during the 2016–19 competitive seasons were retrospectively analyzed for record power outputs (RPOs) and RPOs after prior accumulated work. Results: In JUN, body mass, absolute RPOs, and relative RPOs were higher in HIGHR compared with low ranked (d = 0.97–2.20, large; P = .097–.001); in U23 and PRO, the percentage decrease in RPOs after 20, 30, 40, and 50 kJ·kg⁻¹ was less in HIGHR compared with low ranked (d = 0.77–1.74, moderate–large; P = .096–.004). JUN HIGHR presented lower absolute and relative RPO-20 min (${\eta }_{\mathrm{p}}^2=.34-.38$, large; P = .099–.001) and higher percentage decrease in RPOs after prior accumulated work compared with U23 and PRO HIGHR (${\eta }_{\mathrm{p}}^2=.28-.68$, large; P = .060–.001); percentage decrease in RPOs after prior accumulated work was the only parameter differentiating U23 and PRO HIGHR, with PRO declining less in relative RPO-1 min, RPO-5 min, and RPO-20 min after 20 to 50 kJ·kg⁻¹ (${\eta }_{\mathrm{p}}^2=.28-.68$, large; P = .090–.001). Conclusions: Superior absolute and relative RPOs characterize HIGHR JUN climbing specialists. Superior fatigue resistance differentiates HIGHR U23 and PRO climbers compared with low ranked, as well as PRO versus U23 climbers.