Hypoxic exposure with high intensity interval training has demonstrated an effective improvement in sports performance by inducing specific physiological adaptation, whereas there is limited evidence regarding the influence of repeated exposure to hypoxic training on sports performance. Therefore, this study aims to investigate the effect of repeated hypoxic exposure with high intensity interval training (HIIT) on trained athletes. Seventeen male trained athletes (age = 26.7 ± 5.9 yrs; height = 172.1 ± 8.7 cm; weight = 70.3 ± 10.1 kg; BMI = 23.7 ± 3.1 kg/m2) were recruited and they were divided into two groups based on their previous hypoxic training experience: (i) Experienced Group, EG (n = 10): participants who have experienced RSH training before, followed by a 4-weeks of washout period after the training program; (ii) Non-experienced Group, NEG (n = 7): participants who have no previous exposure to the RSH training program. The participants underwent a 4-week cycling repeated sprint hypoxia training program, during which jump performance, speed, anaerobic capacity, aerobic capacity, and repeated sprint ability (RSA) before and after the training were measured. Results showed that only aerobic capacity improved significantly in EG (p = 0.038) while the NEG showed significant improvement in measures (peak power: p = 0.017; average power: p = 0.002; and RSA: p = 0.011). After 4 weeks of training, there was no change in jump performance or speed, regardless of group. In conclusion, a single block of 4-weeks RSH training exposure is sufficient in improving sport performance while repeated exposure only improves aerobic capacity but not in jumping performance and speed.