The patient is a 65-year-old female recreational skier and avid walker who presented with a several-month history of right ankle and foot pain. The patient's pain began without inciting event and was described as a constant aching pain aggravated by downhill walking and alleviated with rest. She was diagnosed with right distal tibialis anterior tendinopathy with partial thickness tear noted on magnetic resonance imaging and musculoskeletal ultrasound. Given symptoms recalcitrant to conservative measures, the patient opted to pursue an ultrasound-guided prolotherapy injection and a course of physical therapy; unfortunately, she did not have any improvement in symptoms. The patient subsequently underwent ultrasound-guided percutaneous ultrasonic tenotomy and debridement of the distal tibialis anterior tendon, followed by a postprocedure rehabilitation protocol of physical therapy with transition to home exercise program with complete resolution of her pain. Prolotherapy, and percutaneous ultrasonic tenotomy and debridement are two treatment modalities that show promise in the treatment of painful, chronic tendinopathy.