Rolling-element bearings (REB) can develop severe damage due to skidding (slipping) between the rolling elements and bearing races. Skidding can be described as gross sliding between the bearing surfaces in relative motion and can result in significant surface distress such as smearing, especially at light loads and high rotational speeds. Under these conditions, skidding occurs between the rolling elements and the bearing races, leading to increased wear (higher friction coefficient), elevated bearing temperature, significant power losses, and reduced service life of the bearing. The main objective of this study is to investigate the significance of various sensing technologies (induction, vibration, ultrasound, acoustic, and optical) in detecting skidding in standard series roller bearings as well as custom-made roller bearings for aero-engine applications. The bearings have a bore diameter of 60 mm and 90 mm, respectively. Jet and under-race lubrication techniques have been used to supply oil to the bearings under test. The custom-made aero-engine test bearing features special channels to allow under-race lubrication of the rollers/races contacts as well as the cage land. The effect of radial load, rotational speed, and oil flow on roller skidding have also been investigated and analyzed. Tests have been performed on a dedicated high-speed experimental bearing facility and data was recorded using a commercially available data acquisition system.