Tendinopathy is frequently associated with structural disorganization within the tendon. As such, the clinical use of ultrasound and magnetic resonance imaging for tendinopathy has been the focus of numerous academic studies and clinical discussions. However, similar to other musculoskeletal conditions (osteoarthritis and intervertebral disc degeneration), there is no direct link between tendon structural disorganization and clinical symptoms, with findings on imaging potentially creating a confusing clinical picture. While imaging shows the presence and extent of structural changes within the tendon, the clinical interpretation of the images requires context in regard to the features of pain and the aggravating loads. This review will critically evaluate studies that have investigated the accuracy and sensitivity of imaging in the detection of clinical tendinopathy and the methodological issues associated with these studies (subject selection, lack of a robust gold standard, reliance on subjective measures). The advent of new imaging modalities allowing for the quantification of tendon structure or mechanical properties has allowed new critical insight into tendon pathology. A strength of these novel modalities is the ability to quantify properties of the tendon. Research utilizing ultrasound tissue characterization and sonoelastography will be discussed. This narrative review will also attempt to synthesize current research on whether imaging can predict the onset of pain or clinical outcome, the role of monitoring tendon structure during rehabilitation (ie, does tendon structure need to improve to get a positive clinical outcome?), and future directions for research, and to propose the clinical role of imaging in tendinopathy.