We aimed to (i) determine self-reported injury and illness frequency in trail runners 4 weeks preceding competition; (ii) compare athletes with and without injury/illness by sex, age, body mass index (BMI) and competition distance; (iii) describe mechanism of injury, anatomical region (injury)/organ system (illness) involved, consequences of injury on preparation and self-perception of injury severity; (iv) compare anatomical region (injury) and organ system (illness) by sex. A total of 654 trail runners (age 36.2, IQR 30.6–43.0; 36.9% females) participated in this retrospective cross-sectional study by completing a self-reported questionnaire. Injury and illness frequency rates were 31.3% (n = 205, CI: 27.7–35.0%) and 22.3% (n = 146, CI: 19.1–25.7%), respectively. No significant difference was found between injured vs. non-injured or ill vs. non-ill study participants by sex, age, BMI and competition distance. Regarding injuries, gradual onset (41.6%) and knee (33.2%) were the most indicated mechanism and anatomical region of injury. At least 85.4% of trail runners changed their training following injury and 79% indicated that their injury would affect their competition performance. Regarding illness, the respiratory tract was the most frequent organ system involved (82.9%). Male and female participants reported similar proportions of anatomical regions (injury) and organ systems (illness) affected. These results could help to generate education strategies and appropriate medical support before and during these competitions.