Lateral digital flexor tendonitis is a rarely reported cause of hind limb lameness in performance horses. The purpose of this retrospective study was to describe clinical and diagnostic imaging findings for a group of horses with lateral digital flexor tendinitis within the tarsal sheath. Equine cases with a diagnosis of lateral digital flexor tendonitis and magnetic resonance imaging (MRI) studies of the affected region were retrieved from North Carolina University’s medical record database. Recorded data for included horses were signalment; findings from history, physical examination, lameness examination, and all diagnostic imaging studies; treatment administered; and outcome. Four horses met inclusion criteria. Lameness was mild/moderate in severity and insidious in onset in all patients. Responses to flexion tests were variable. All horses showed positive improvement(70–90%) in lameness after tarsal sheath analgesia. Radiographic, scintigraphic, and ultrasonographic findings were inconclusive. For all horses, MRI characteristics included increased T2, PD, and STIR signal intensity within the lateral digital flexor tendon in the area of the tarsal sheath. Tarsal sheath effusion was slight in three horses, and mild/moderate in one horse. With medical treatment, two horses were sound at 6-month follow up, one horse was sound at 1-year followup, and one horse had a slight persistent lameness (grade 1/5) at 9-month followup. Findings supported the use of MRI for diagnosing lateral digital flexor tendonitis within the tarsal sheath in horses. Affected horses may have a good prognosis for return to athletic performance following appropriate medical treatment.