The purpose of this study was to examine changes in running performance and physical qualities related to middle-distance performance over a training season. The study also examined relationships between training loading and changes in physical qualities as assessed by laboratory and field measures. Relationships between laboratory and field measures were also analyzed. This was a 9-month observational study of 10 highly trained adolescent middle-distance athletes. Training intensity distribution was similar over the observational period, whereas accumulated and mean distance and training time and accumulated load varied monthly. Statistically significant (p < 0.05) and large effect sizes (Cohen's d) (>0.80) were observed for improvements in: body mass (5.6%), 600-m (4.6%), 1,200-m (8.7%), and 1,800-m (6.1%) time trial performance, critical speed (7.1%), V[Combining Dot Above]O2max (5.5%), running economy (10.1%), vertical stiffness (2.6%), reactive index (3.8%), and countermovement jump power output relative to body mass (7.9%). Improvements in 1,800 m TT performance were correlated with increases in V[Combining Dot Above]O2max (r = 0.810, p = 0.015) and critical speed (r = 0.918, p = 0.001). Increases in V[Combining Dot Above]O2max and critical speed were also correlated (r = 0.895, p = 0.003). Data presented here indicate that improvements in critical speed may be reflective of changes in aerobic capacity in adolescent middle-distance athletes.