PURPOSE: To compare the effect of a 20-minute nap opportunity (N20), a moderate dose of caffeine (CAF; 5 mg·kg-1), or a moderate dose of caffeine before N20 (CAF+N) as possible countermeasures to the decreased performance and the partial sleep deprivation-induced muscle damage. METHODS: Nine male, highly trained judokas were randomly assigned to either baseline normal sleep night, placebo, N20, CAF, or CAF+N. Test sessions included the running-based anaerobic sprint test, from which the maximum (Pmax), mean (Pmean), and minimum (Pmin) powers were calculated. Biomarkers of muscle, hepatic, and cardiac damage and of enzymatic and nonenzymatic antioxidants were measured at rest and after the exercise. RESULTS: N20 increased Pmax compared with placebo (P < .01, d = 0.75). CAF+N increased Pmax (P < .001, d = 1.5; d = 0.94), Pmin (P < .001, d = 2.79; d = 2.6), and Pmean (P < .001, d = 1.93; d = 1.79) compared with placebo and CAF, respectively. Postexercise creatine kinase increased whenever caffeine was added, that is, after CAF (P < .001, d = 1.19) and CAF+N (P < .001, d = 1.36). Postexercise uric acid increased whenever participants napped, that is, after N20 (P < .001, d = 2.19) and CAF+N (P < .001, d = 2.50) and decreased after CAF (P < .001, d = 2.96). CONCLUSION: Napping improved repeated-sprint performance and antioxidant defense after partial sleep deprivation. Contrarily, caffeine increased muscle damage without improving performance. For sleep-deprived athletes, caffeine before a short nap opportunity would be more beneficial for repeated sprint performance than each treatment alone.