A Bartholin gland drainage catheter, a method of using the drainage catheter, and a kit containing a drainage catheter are disclosed. The drainage catheter comprises a shaft having an external diameter, a proximal end and a distal end and a drainage lumen extending between the respective ends. The distal end of the shaft comprises a retention mechanism, such as a Malecot, having a plurality of expandable wings which anchor the catheter within the Bartholin gland. The wings are selectively moveable from a first radially expanded position to a second radially compressed insertion position. The proximal end of the catheter shaft comprises an anchoring element having an external diameter that is greater than the external diameter of the shaft which remains outside of the patients labial tissue. The catheter is inserted into the gland with the Malecot retained in a compressed configuration, and then subsequently allowed to expand within the gland, thus securing the catheter in place to facilitate drainage and healing of a cystic gland.