The aim of this study was to compare barbell velocities at different intensities and estimated 1-RM with actual 1-RM measured with different measuring tools in bench presses and squats. Fourteen resistance-trained athletes (eight men, six women, age 28.1 ± 7.5 years, body mass 78.1 ± 12.2 kg, body height 1.73 ± 0.09 m) performed bench presses and squats at five loads varying from 45 to 85% of one repetition maximum (1-RM), together with 1-RM testing, while measuring mean, mean propulsive, and peak barbell velocity with six different commercially used inertial measurement units (IMUs) and linear encoder software systems attached to the barbell. The 1-RM was also estimated based upon the load–velocity regression, which was compared with the actual 1-RM in the bench press and squat exercises. The main findings were that GymAware revealed the highest reliability along with minimal bias, while Musclelab and Vmaxpro showed moderate reliability with some variability at higher loads. Speed4lifts and PUSH band indicated greater variability, specifically at higher intensities. Furthermore, in relation to the second aim of the study, significant discrepancies were found between actual and estimated 1-RM values, with Speed4lifts and Musclelab notably underestimating 1-RM. These findings underscore the importance of selecting reliable tools for accurate velocity-based training and load prescription.