Objective: To determine the associations between training load, baseline characteristics (e.g. age or previous injury) and rate of musculoskeletal injury and/or pain specifically within an Endurance Sporting Population (ESP). Design: Prospectively registered systematic review. 3 Methods: Eight electronic databases were searched by two independent reviewers. Studies were required to prospectively monitor both (i) training loads and (ii) musculoskeletal injury and/or pain for >3 months. Methodological quality and risk of bias were determined utilising the Critical Skills Appraisal Program (CASP). Reported effect sizes were categorised as small, medium or large. Results: Twelve endurance sport studies were eligible (running, triathlon, rowing). Increased injury and/or pain risk was associated with: (i) high total training distances per week/month (medium effect size) (ii) training frequency <2 sessions/week (medium effect size) and (iii) both low weekly (<2 hours/week) and high monthly (large effect size) training durations. None of the studies reported internal training load data or acute:chronic workload ratios. Baseline characteristics found to increase the rate of injury and/or pain included: (i) a history of previous injury (medium effect size), (ii) age >45 years (small effect size), (iii) non-musculoskeletal comorbidities (large effect size), (iv) using older running shoes (small effect size) and (v) non-competitive behaviour. Conclusions: This review identifies a range of external training load factors and baseline characteristics associated with an increased rate of injury and/or pain within ESPs. There is an absence of research relating to internal training loads and acute:chronic workload ratios in relation to rate of injury and/or pain within ESPs.