Work-related musculoskeletal pain (MSP) risk assessments by trained observers are often used in ergonomic practice; however, the validity may be questionable. We investigated the predictive value of work-site MSP risk estimates in a prospective cohort study of 1745 workers. Trained observers estimated the risk of MSP (neck, shoulder or low-back pain) using a three-point scale (high, moderate and low risk) after observing a video of randomly selected workers representing a task group. Associations of the estimated risk of pain and reported pain during a three-year follow-up were assessed using logistic regression. Estimated risk of neck and shoulder pain did (odds ratio, OR: 1.45 (95% confidence interval, CI: 1.01-2.08); 1.64 (95% CI: 1.05-2.55)), however, estimated risk of low-back pain did not significantly predict pain (OR: 1.27 (95% CI: 0.91-1.79)). The results show that observers were able to estimate the risk of shoulder and neck pain, whereas they found it difficult to estimate the risk of low-back pain. Practitioner Summary: Work-related musculoskeletal pain risk assessments by observers are often used in ergonomic practice. We showed that observers were able to estimate shoulder and neck pain risk, but had difficulties to estimate the risk of low-back pain. Therefore, observers' risk estimates might provide a useful method for musculoskeletal pain risk assessments.