A catheter anchoring system, apparatus and method for securing a catheter to a patients skin, having two flexible side members and a cross-member therebetween to which a retaining assembly is mounted. The retaining assembly may hold a catheter hub at an angle for patient comfort. Gripping tabs secure to each retaining assembly side are gripped while advancing a cannula guide needle into the patients vein and while attaching the catheter hub to a medical accessory, such as intravenous (I.V.) tubing, for increased patient comfort, reduction of the risk in contamination and patient infection, and to more easily and quickly start an I.V.