Purpose: To determine the association between training-load (TL) factors, baseline characteristics, and new injury and/or pain (IP) risk in an endurance sporting population (ESP). Methods: Ninety-five ESP participants from running, triathlon, swimming, cycling, and rowing disciplines initially completed a questionnaire capturing baseline characteristics. TL and IP data were submitted weekly over a 52-wk study period. Cumulative TL factors, acute:chronic workload ratios, and exponentially weighted moving averages were calculated. A shared frailty model was used to explore time to new IP and association to TL factors and baseline characteristics. Results: 92.6% of the ESP completed all 52 wk of TL and IP data. The following factors were associated with the lowest risk of a new IP episode: (a) a low to moderate 7-d lag exponentially weighted moving averages (0.8–1.3: hazard ratio [HR] = 1.21; 95% confidence interval [CI], 1.01–1.44; P = .04); (b) a low to moderate 7-d lag weekly TL (1200–1700 AU: HR = 1.38; 95% CI, 1.15–1.65; P < .001); (c) a moderate to high 14-d lag 4-weekly cumulative TL (5200–8000 AU: HR = 0.33; 95% CI, 0.21–0.50; P < .001); and (d) a low number of previous IP episodes in the preceding 12 mo (1 previous IP episode: HR = 1.11; 95% CI, 1.04–1.17; P = .04). Conclusions: To minimize new IP risk, an ESP should avoid high spikes in acute TL while maintaining moderate to high chronic TLs. A history of previous IP should be considered when prescribing TLs. The demonstration of a lag between a TL factor and its impact on new IP risk may have important implications for future ESP TL analysis.