Background: Prior studies have revealed magnetic resonance imaging (MRI) evidence of elbow pathology in single-season evaluation of competitive youth baseball players. The natural history of these findings and risk factors for progression have not been reported. Purpose: To characterize the natural history of bilateral elbow MRI findings in a 3-year longitudinal study and to correlate abnormalities with prior MRI findings, throwing history, playing status, and physical examination. Study Design: Cohort study; Level of evidence, 2. Methods: A prospective study of Little League players aged 12 to 15 years was performed. All players had preseason and postseason bilateral elbow MRI performed 3 years before this study. Players underwent repeat bilateral elbow MRI, physical examination, and detailed assessment of throwing history, playing status, and arm pain. Imaging was read by a blinded musculoskeletal radiologist and compared with prior MR images to assess for progression or resolution of previously identified pathology. Results: All 26 players who participated in the previous single-season study returned for a 3-year assessment. At the completion of the study, 15 players (58%) had dominant arm MRI pathology. Eighty percent (12/15 players) of MRI findings were new or progressive lesions. Players with postseason MRI pathology at the beginning of the study were more likely to have MRI pathology at the 3-year follow-up than players with previously normal postseason MRI ( P < .05), although 6 of the 14 players (43%) with previously normal MRI developed new pathology. Year-round play was a significant predictor of tenderness to elbow palpation ( P = .027) and positive MRI findings at 3 years ( P = .047). At the 3-year follow-up, 7 players (27%) reported having throwing elbow pain and 3 had required casting. Additionally, differences were noted in the dominant arm’s internal and external rotation in those that continued to play baseball ( P < .05). Conclusion: Dominant elbow MRI abnormalities are common in competitive Little League Baseball players. Year-round play imparts significant risk for progression of MRI pathology and physical examination abnormalities.