Deep digital flexor (DDF) tendinopathy is one of the most frequent causes of foot lameness and the prognosis is guarded. The progress of lesion healing may be followed by magnetic resonance (MR) imaging to formulate a prognosis and to adapt the rehabilitation program. We assessed the correlation of outcome with total tendon damage and temporal resolution of MR abnormalities. Images from 34 horses with DDF tendinopathy that had undergone at least two low-field standing MR examinations of the foot (mean 2.5 ± 1.3 times) were reviewed. No horse having a T1-GRE hyperintense lesion over 30 mm in length or over 10% tendon cross-sectional area returned to its previous activity level. Horses with concomitant lesions had worse outcome than horses with DDF tendinopathy only (P = 0.005). In all horses including those with excellent outcome, the lesion persisted, even mildly, in T1-GRE and PD images. Horses with tendon lesion resolution on STIR-FSE and T2-FSE images on recheck examination had a better outcome (P = 0.0004 and P = 0.002, respectively), and all horses that returned to their previous level of performance had complete resolution of signal hyperintensity on the STIR-FSE sequence. Although rehabilitation remains multifactorial, characteristics of DDF tendinopathy and concomitant lesions on first and recheck MR examinations allow refining the prognosis.