This study proposes a statistical approach based on vibration energy at damage to detect multiple damages occurring in roller bearings. The analysis was performed at four different rotating speeds—1002, 1500, 2400, and 3000 RPM—following four different damages—inner race, outer race, ball, and combination damage—and under two types of loading conditions. These experiments were performed on a SpectraQuest Machinery Fault Simulator™ by acquiring the vibration data through accelerometers under two operating conditions: with the bearing loader on the rotor shaft and without the bearing loader on the rotor shaft. The histograms showed diversity in the defected bearing as compared to the intact bearing. There was a marked increase in the kurtosis values of each damaged roller bearing. This research article proposes that histograms, along with kurtosis values, represent changes in vibration energy at damage that can easily detect a damaged bearing. This study concluded that the vibration energy at damage-based statistical technique is an outstanding approach to detect damages in roller bearings, assisting Industry 4.0 to diagnose faults automatically.