The purposes of this study were to determine the validity and test-retest reliability of the 1 repetition maximum (1RM) chain-loaded, free-weight bench press (CBP) and to examine possible learning effects that may occur between the test-retest measurements. Nine resistance-trained men (20.58 ± 1.31 years, 188.24 ± 9.29 cm, 92.07 ± 16.94 kg) and seven resistance-trained women (20.42 ± 0.98 years, 175.61 ± 9.32 cm, 73.61 ± 10.80 kg) participating in Division II college basketball completed this study. Two familiarization sessions took place using light to moderate loads to learn proper technique. The subjects completed a 1RM test on the traditional plate-loaded bench press 4 days before completion of the CBP 1RM, which was followed by 4 days of rest before completing the retest. Intraclass correlation coefficients (ICC) and the percent coefficients of variation (CV) were used to determine relative and absolute test-retest reliability. Concurrent validity was determined from the Pearson correlation coefficients between the CBP and the plate-loaded bench press. Test-retest differences were analyzed with the paired t-test. ICC and CV for the men (r = 0.99, 1.4%) and women (r = 0.93, 3.5%), respectively indicate that highly reproducible 1RM scores can be found with the CBP. High validity was also found with high correlations between the CBP and plate-loaded bench press for the men (r = 0.95) and women (r = 0.80). A statistically significant (p = 0.04) but clinically small (2.57 kg) shift in the mean occurred between the CBP test and retest for the men, whereas no change occurred for the women. The data indicate that valid and reliable 1RM scores can be found after two familiarization sessions in men and women athletes who have previous resistance training experience.