Clinical disease from otitis media in calves is a significant problem in the dairy industry and evaluation of disease severity, chronicity, and imaging remains a challenge. Our objectives were to compare imaging findings in calves with an early diagnosis of respiratory disease to calves with treatment failure. This was a prospective study of 30 Jersey heifer calves, 26-95 days of age, with elevated clinical respiratory scores. Ten clinically healthy calves served as controls for clinical scoring. Three groups of calves were selected based on elevated scores using the McGuirk respiratory scoring system and treatment history. Group A included new cases, group B included primary treatment failures, and group C included multiple treatment failures. Calves underwent a skull CT, four view radiography, post-mortem photography of the tympanic bulla and bacteriological diagnostics. Imaging and post-mortem results were evaluated using normalized scoring schemes. Computed tomography imaging of the tympanic bulla differentiated calves early in the course of disease (group A) from calves that had not responded to treatment (groups B and C). Radiographs differentiated only group C from groups A and B. Use of a 35 degree angle dorsal-right or dorsal-left ventral oblique projection for radiography allowed effective evaluation of the tympanic bulla. Clinical respiratory scores were similar among all three groups. Computed tomography imaging can differentiate early from advanced otitis media. Radiographs, which can be performed in the field, also have utility to identify advanced otitis media to aid management decisions.