Athletes at risk for valgus extension overload are also at risk for tears of the anterior bundle of the ulnar collateral ligament. Some athletes develop ligament tears after procedures for valgus extension overload such as posteromedial olecranon osteotomy. The amount of posteromedial olecranon that can be resected before ulnar collateral ligament strain, and risk of injury, increases is unknown. We dissected and mounted five fresh-frozen human cadaveric elbows to allow strain gauge monitoring of the ulnar collateral ligament with varying valgus stress, elbow flexion angle, and medial osteotomy. The average strain to failure was 11.96% ± 6.51%, corresponding to a load of 347.71 ± 46.42 N. The maximum tensile force recorded at failure was 416.24 N. Three-way repeated-measures analysis of variance revealed no significant change in strain with change in the amount of osteotomy for a given applied load and angle of flexion. On the basis of these data, we conclude that the effect of medial olecranon osteotomy on ulnar collateral ligament strain may be small. Small sample size, elderly specimens, and the variables inherent in the experimental setup and mathematical modeling make it difficult to extrapolate these results to in vivo behavior of the anterior ulnar collateral ligament. Further work is needed before definitive guidelines for olecranon osteotomy can be formulated.