Purpose: To examine the relationship between player internal workloads, daily wellness monitoring, and injury and illness in a group of elite adolescent cricketers during overseas competitions. Methods: A total of 39 male international adolescent cricketers (17.5 [0.8] y) took part in the study. Data were collected over 5 tours across a 3-y period (2014–2016). Measures of wellness were recorded and daily training loads were calculated using session rating of perceived exertion. The injury and illness status of each member of the squad was recorded daily. Acute and chronic workloads were calculated using 3-d and 14-d moving averages. Acute workloads, chronic workloads, and acute chronic workload ratios were independently modeled as fixed effects predictor variables. Results: In the subsequent week, a high 3-d workload was significantly associated with an increased risk of injury (relative risk = 2.51; CI = 1.70–3.70). Similarly, a high 14-d workload was also associated with an increased risk of injury (relative risk = 1.48; CI = 1.01–2.70). Individual differences in the load–injury relationship were also found. No clear relationship between the acute chronic workload ratios and injury risk was found, but high chronic workloads combined with high or low acute chronic workload ratios showed an increased probability of injury compared with moderate chronic workloads. There were also trends for sleep quality and cold symptoms worsening the week before an injury occurred. Conclusion: Although there is significant individual variation, short-term high workloads and change in wellness status appear to be associated with injury risk.