Anchors for securing a medical device relative to a burr hole, wherein the anchors may accommodate most any implantation trajectory through the burr hole. Such anchors may further secure the device along any such trajectory without imparting undesirable biasing forces that may shift the device from its intended implanted location. In some embodiments, the anchor is configured with a cup-shaped retention member through which the medical device passes. The retention member may receive a volume of curable material therein to provide strain relief to the medical device.