A surgical sleeve is disclosed herein for insertion into an opening in tissue to minimize damage to the opening in tissue. The various embodiments of the surgical sleeve include a reinforcement member or a stiffening member for providing radial support to a proximal anchor member. In one embodiment, the surgical sleeve includes a proximal anchor member configured and dimensioned to contact an outer surface of the tissue to inhibit advancement of the surgical sleeve entirely through the opening, a distal anchor member configured and dimensioned to facilitate anchoring of the surgical sleeve within the opening in tissue, a sleeve member extending between the proximal anchor member and the distal anchor member, the sleeve member defining a passageway extending therethrough, and a reinforcement member positionable within the proximal anchor member to provide radial support to the proximal anchor member.