The retrieval tool includes a cylindrical member having a body, an inner passage, a guide cylinder and an engaging member. The engaging member may slide within the cylindrical member in order to frictionally engage a whipstock against an inner surface of the guide cylinder, facilitating removal of the whipstock from a borehole. A actuating member, piston, retainer and swivel sub may be used to connect the engaging member to the retrieval tool and enhance the mobility of the engaging member within the cylindrical member. A spring may also facilitate locking engagement of the engaging member and whipstock. Contact between the retrieval tool and the whipstock may lead to an increase of pressure within the inner passage, such pressure increasing the engagement between the engaging member and whipstock.