Extensor tendinopathy is a degenerative overuse condition involving the common extensor tendon at the lateral humeral epicondyle. The diagnosis and management of this condition are clinically based. Our aims were to determine if through patient history and clinical examination we could ascertain prognostic factors affecting time to symptom resolution in extensor tendinopathy. Symptomatic patients (N = 28) had a thorough history and examination, and rehabilitation monitored regularly for 6 months. Patient outcomes at 6 months were then correlated with specific factors on initial presentation. Factors implicated as having prognostic significance regarding patient outcomes were a current history of manual work (P = 0.04, effect size −0.29), and a current history of weekly participation in racquet sports (P = 0.01, effect size −0.41). These individual factors had a significantly decreased chance of symptom resolution at the 6-month stage, and when combined had an effect size of −0.6 (P = 0.001). Negative patient outcomes may be related to current high and repetitive levels of tendon stress, and rest from recreational and occupational use of wrist extensor tendons may be necessary to enhance the chances of complete symptom resolution. Enforced rest has monetary and quality-of-life implications, but is probably preferable to an incomplete recovery and prolonged tendon pain and dysfunction.