The stick-slip phenomenon widely exists in contact mechanics, from the macroscale to the nanoscale. During cholesteric-nematic unwinding by external fields, there is controversy regarding the role of planar surface anchoring, which may induce discontinuous stick-slip behaviors despite the well-known continuous transitions observed in past experiments. Here we observe three regimes, namely, constrained, stick-slip, and sliding-slip, under mechanical winding with different anchoring conditions, and measure the corresponding forces by the surface force balance. These behaviors result from a balance of cholesteric elastic torque and surface torque, reminiscent of the slip morphology on frictional substrates [T. G. Sano et al., Phys. Rev. Lett. 118, 178001 (2017)10.1103/PhysRevLett.118.178001], and provide evidence of dynamics in static rotational friction.