Purpose: To examine the sleep of rugby league athletes the night before and following an evening match and to investigate the association between caffeine intake and sleep on the night of competition. Methods: On the night prior to, night of, and night after a professional rugby league match, 15 athletes had their sleep monitored using wrist activity monitors. Additionally, saliva samples were collected 60 minutes before and 30 minutes after the competition to assess salivary caffeine concentration. Differences in sleep across the 3 nights were examined using linear mixed models, and changes were assessed using effect size (ES). Pearson correlation (r) assessed the relationship between salivary caffeine levels and sleep indices. Results: On the night of competition, athletes went to bed later than the night before (P = .00002, ES = 1.84) and night after (P = .0003, ES = 1.49) competition. Consequently, their sleep duration was reduced on the night of competition compared with the previous night (P < .0000003, ES = 2.36) and night after competition (P = .001, ES = 1.53). Postcompetition salivary caffeine concentration was substantially elevated in athletes when compared with precompetition measures (P < .00000001, ES = 4.44), and moderate, nonsignificant correlations were observed between changes in salivary caffeine concentration and delayed bedtime (r = .48, P = .07), increased sleep latency (r = .45, P = .09), decreased sleep duration (r = −.30, P = .28), and reduced sleep efficiency (r = −.34, P = .22). Conclusions: These results demonstrate that evening competition results in sleep disturbance in rugby league athletes, and caffeine supplementation prior to and during competition leads to substantial increases in postcompetition salivary caffeine concentration.