High-speed winding of paper web sometimes leads the winding system into unstable states, interlayer slippage of wound roll, paper breakage and so on, due to the excessive air-entrainment at the roll-inlet of nip contact region. Generally, it is known that the amount of air-entrainment is affected by grooving shape of nip roll surface. In this paper, we focused on the grooving shape and investigated the relationship with grooving shape and the amount of air-entrainment at the nip region in order to achieve stable winding at high speed. We conducted experiments using small sized test machine. Entrained air-film thickness was evaluated applying the solution of the elastohydrodynamic lubrication for foil bearing with the consideration of nip profile at the grooved area. Air film thickness was measured to ensure the applicability of the above theory, and the validity of prediction model was confirmed.