Friction and wear behavior exists between hoisting ropes that are wound around the drums of a multi-layer winding hoist. It decreases the service life of ropes and threatens mine safety. In this research, a series of experiments were conducted using a self-made test rig to study the effects of the strand lay direction and crossing angle on the winding rope’s tribological behavior. Results show that the friction coefficient in the steady-state period shows a decreasing tendency with an increase of the crossing angle in both cross directions, but the variation range is different under different cross directions. Using thermal imaging, the high temperature regions always distribute along the strand lay direction in the gap between adjacent strands, as the cross direction is the same with the strand lay direction (right cross contact). Additionally, the temperature rise in the steady-state increases with the increase of the crossing angle in both cross directions. The differences of the wear scar morphology are obvious under different cross directions, especially for the large crossing angle tests. In the case of right cross, the variation range of wear mass loss is larger than that in left cross. The damage that forms on the wear surface is mainly ploughing, pits, plastic deformation, and fatigue fracture. The major wear mechanisms are adhesive wear, and abrasive and fatigue wear.