The present invention provides, in certain aspects, medical systems that are useful for applying bolster material to patient tissue. One such system includes a surgical fastening apparatus that is comprised of a first arm having a first arm working surface; and a cutting element operable along a cutting path. This system also includes at least one piece of bolster material having a portion received in the cutting path, and a retaining element retaining the at least one piece of bolster material in association with the first arm working surface, wherein the retaining element has one or more segments received in the cutting path and includes portions residing between the first arm working surface and the at least one piece of bolster material. The invention also provides medical devices that are useful for applying bolster materials to surgical fastening apparatuses, as well as methods for preparing and using such devices.