Background: Plantar heel pain (PHP) is a common musculoskeletal disorder, with both extracorporeal shockwave therapy (ESWT) and specific exercise such as plantar fascia specific stretching shown to be effective treatments. This review aimed to evaluate the effectiveness of combined ESWT and exercise interventions versus other interventions in treating PHP. Methods: A systematic review of effectiveness was conducted, adhering to the PRISMA guidelines. Five databases were searched for studies published between January 2000 and March 2020, with 12 studies meeting the inclusion criteria. The Grading of Recommendations Assessment Development and Evaluation (GRADE) framework was used to determine quality of recommendations. Results: The 12 included studies (n = 861) compared ESWT and stretching with various other treatments. Due to clinical and methodological heterogeneity, pooling of data was not possible, and a narrative synthesis of findings was provided. There was high quality evidence that combined ESWT and stretching interventions are more effective than those using either alone or botulinum toxin injections, and low-quality evidence of superiority versus ultrasound and stretching. There was moderate quality evidence that combined ESWT and stretching is no more effective than corticosteroid injection (CSI), and high quality evidence that the combination is no more effective than blood-derived injection therapies, custom orthotics or low-level laser therapy (LLLT) combined with stretching. There is high quality evidence that the use of topical corticosteroid or laser therapy in combination with ESWT and stretching increases effectiveness compared to ESWT and stretching alone, and moderate quality evidence for the additive effective of dry needling. Conclusions: Combined ESWT and stretching treatments are effective and may be recommended where they are available and practical to implement. Further high-quality studies with larger sample sizes and longer follow-up durations comparing combined interventions for PHP, including different exercise types such as resistance training are required.