The purpose of our study was to determine differences in adaptative and injury patterns in the elbow related to valgus extension overload (VEO) in overhead throwing athletes by age. A total of 86 overhead throwing athletes and 23 controls underwent MRI or MR arthrography (MRA) of the elbow. Throwing athletes were divided by age into three groups: ≤16 years (26 subjects), 17–19 years (25 subjects), and ≥20 years (35 subjects). Consensus interpretation of each MRI was performed, with measurements of ulnar collateral ligament (UCL) thickness and subchondral sclerosis at the radial head, humeral trochlea, and olecranon process. A higher frequency of apophyseal and stress injuries was seen in adolescent athletes and increased incidence of soft tissue injuries was observed in older athletes. Early adaptive and degenerative changes were observed with high frequency independent of age. Significant differences were observed between athletes and controls for UCL thickness (p < 0.001) and subchondral sclerosis at the radial head (p < 0.001), humeral trochlea (p < 0.001), and olecranon process (p < 0.001). Significant differences based on athlete age were observed for UCL thickness (p < 0.001) and subchondral sclerosis at the olecranon process (p = 0.002). Our study highlights differences in anatomic adaptations related to VEO at the elbow between overhead throwing athletes and control subjects, as well as across age in throwing athletes.